Substituted 2-benz(o)ylpyridines, their preparation and their use as herbicides

ABSTRACT

Substituted 2-benz(o)ylpyridines I                    
     and salts thereof where 
     n=0, 1; 
     X=CO, CH 2 , CH(C 1 -C 4 -alkyl), CH—OH, CH—CN, CH-halogen, C(halogen) 2 , CH—CONH 2 , CH—CO—O(C 1 -C 4 -alkyl), CH—O(C 1 -C 4 -alkyl), C(CN)(C 1 -C 4 -alkyl); 
     R 1 =halogen, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl; 
     R 2 =H, halogen; 
     R 3 =H, NO 2 , OH, halogen, C 1 -C 4 -alkoxy; 
     R 4 =H, NO 2 , OH, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy; 
     R 5 =H, NO 2 , CN, halogen, C 1 -C 8 -alkyl, C 3 -C 8 -alkenyl, C 3 -C 8 -alkynyl, C 3 -C 8 -cycloalkyl, C 1 -C 8 -haloalkyl, C 2 -C 8 -haloalkenyl, C 2 -C 8 -haloalkinyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 2 -C 4 -alkenyloxy-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyloxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, C 1 -C 4 -alkylsulfinyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylsulfonyl-C 1 -C 4 -alkyl, cyano-C 1 -C 8 -alkyl, cyano-C 2 -C 8 -alkenyl, cyano-C 3 -C 8 -alkynyl, unsubstituted or substituted OH, SH, SO—H, —SO 2 —H, COOH or NH—COOH, —SO 2 Cl, —N(R 9 ,R 10 ), —NH—SO 2 —(C 1 -C 8 -alkyl), —N[—SO 2 —(C 1 -C 8 -alkyl)] 2 , —N(C 1 -C 8 -alkyl)[—SO 2 —(C 1 -C 8 -alkyl)], —SO 2 —N(R 9 ,R 10 ), —O—CO—NH—R 9 , unsubstituted or substituted CHO, —O—CHO or —NH—CHO, —NH—CO—NH—R 9 , —O—CS—NH 2 , —O—CS—N(C 1 -C 8 -alkyl) 2 , —CO—N(R 9 ,R 10 ), —CS—N(R 9 ,R 10 ), —CO—NH—SO 2 —(C 1 -C 4 -alkyl).

CROSS-REFERENCE

This application is a § 371 of PCT/EP98/01354 filed Mar. 09, 1998.

The present invention relates to novel substituted 2-benz(o)ylpyridinesof the formula I

where

n is 0 or 1;

X is carbonyl, methylene, CH(C₁-C₄-alkyl), CH—OH, CH—CN, CH-halogen,C(halogen)₂, CH—CONH₂, CH—CO—O(C₁-C₄-alkyl), CH—O(C₁-C₄-alkyl) or C(CN)(C₁-C₄-alkyl);

R¹ is halogen, C₁-C₄-haloalkyl, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl orC₁-C₄-alkylsulfonyl;

R² is hydrogen or halogen;

R³ is hydrogen, nitro, hydroxyl, halogen, or C₁-C₄-alkoxy;

R⁴ is hydrogen, nitro, hydroxyl, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkylor C₁-C₄-alkoxy;

R⁵ is hydrogen, nitro, cyano, halogen, C₁-C₈-alkyl, C₃-C₈-alkynyl,C₃-C₈-alkynyl, C₃-C₈-cycloalkyl, C₁-C₈-haloalkyl, C₂-C₈-haloalkenyl,C₂-C₈-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₂-C₄-alkenyloxy-C₁-C₄-alkyl, C₂-C₄-alkynyloxy-C₁-C₄-alkyl,C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkylsulfinyl-C₁-C₄-alkyl,C₁-C₄-alkylsulfonyl-C₁-C₄-alkyl, cyano-C₁-C₈-alkyl, cyano-C₂-C₈-alkenyl,cyano-C₃-C₈-alkynyl, —OR⁸, —SR⁸, —SO—R⁸, —SO₂—R⁸, —SO₂Cl, —N(R⁹,R¹⁰),—NH—SO₂—(C₁-C₈-alkyl), —N[—SO₂—(C₁-C₈-alkyl)]₂,—N(C₁-C₈-alkyl)[—SO₂—(C₁-C₈-alkyl)], —SO₂—N(R⁹,R¹⁰), —N(R¹¹)—CO—R¹²,—NH—CO—OR⁸, —O—CO—NH—R⁹, —O—CO—R¹², —NH—CO—NH—R⁹, —O—CS—NH₂,—O—CS—N(C₁-C₈-alkyl)₂, —CO—OR⁸, —CO—N(R⁹,R¹⁰), —CS—N(R⁹,R¹⁰),—CO—NH—SO₂—(C₁-C₄-alkyl), —CO—N(C₁-C₄-alkyl)—SO₂—(C₃-C₄-alkyl), —CO—R¹²,hydroxycarbonyl-C₁-C₈-alkyl, (C₁-C₈-alkoxy)carbonyl-C₁-C₆-alkyl,—CH₂—CH(halogen)—CO—OR⁸, —CH₂—CH(halogen)—CO—N(R⁹,R¹⁰),—CH₂—CH(halogen)—CN, —CH₂—CH(halogen)—CO—(C₁-C₄-alkyl),—CH═C(halogen)—CO—OR⁸, —CH═C(C₁-C₄-alkyl)—CO—OR⁸, —CH═N—OR¹³,—C(R¹⁴)═N—OR¹³, —CH(—Y—R¹⁵, —Z—R¹⁵), —C(R¹⁴)(—Y—R¹⁵, —Z—R¹⁵),

R⁸ is hydrogen, C₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₁-C₈-haloalkyl,cyano-C₁-C₈-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkylsulfinyl-C₁-C₄-alkyl,C₁-C₄-alkylsufdonyl-C₁-C₄-alkyl, C₃-C₈-alkenyl, C₅-C₈-cycloalkenyl,C₃-C₈-haloalkenyl, C₃-C₈-alkynyl, hydroxycarbonyl-C₁-C₄-alkyl,(C₁-C₈-alkoxy)carbonyl-C₁-C₆-alkyl,(C₃-C₈-alkenyloxy)carbonyl-C₁-C₆-alkyl,(C₃-C₈-alkynyloxy)carbonyl-C₁-C₆-alkyl,C₁-C₄-alkoxy-(C₁-C₄-alkoxy)carbonyl-C₁-C₄-alkyl,(C₁-C₈-haloalkoxy)carbonyl-C₁-C₆-alkyl,C₃-C₈-cycloalkyloxy)carbonyl-C₁-C₆-alkyl,(C₁-C₄-alkoxy)carbonyl-(C₁-C₄-alkoxy)carbonyl-C₁-C₄-alkyl,(C₃-C₆-alkenyloxy)carbonyl-C₁-C₄-alkoxy)carbonyl-C₁-C₄-alkyl,(C₃-C₆-alkynyloxy)carbonyl-(C₁-C₄-alkoxy)carbonyl-C₁-C₄-alkyl,hydroxycarbonyl-(C₁-C₄-alkoxy)carbonyl-C₁-C₄-alkyl,oxetan-3-yloxycarbonyl-C₁-C₄-alkyl, phenoxycarbonyl-C₁-C₄-alkyl, benzylor benzyloxycarbonyl-C₁-C₄-alkyl, where each of the phenyl rings of thelast 3 radicals may be unsubstituted or may carry one to threesubstituents, in each case selected from the group consisting of nitro,cyano, hydroxyl, hydroxycarbonyl, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, (C₁-C₄-alkoxy)carbonyl and(C₁-C₄-alkoxy)carbonyl-C₁-C₄-alkoxy;

R⁹ and R¹⁰ independently of one another are each hydrogen, C₁-C₈-alkyl,C₃-C₈-cycloalkyl, C₃-C₈-alkenyl, C₃-C₈-alkynyl, C₁-C₈-haloalkyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl,C₁-C₄-alkylsulfinyl-C₁-C₄-alkyl, C₁-C₄-alkylsulfonyl-C₁-C₄-alkyl,cyano-C₁-C₈-alkyl, hydroxycarbonyl-C₁-C₄-alkyl,(C₁-C₄-alkoxy)carbonyl-C₁-C₄-alkyl,(C₃-C₇-cycloalkyloxy)carbonyl-C₁-C₄-alkyl,(C₁-C₄-alkoxy)carbonyl-C₃-C₇-cycloalkyl,C₁-C₄-alkoxy-(C₁-C₄-alkoxy)carbonyl-C₁-C₄-alkyl, C₁-C₆-alkoxy, phenyl orphenyl-C₁-C₄-alkyl, where the phenyl rings of the last two radicals maybe unsubstituted or may carry one to three substituents, in each caseselected from the group consisting of nitro, cyano, hydroxyl, halogen,C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, (C₁-C₄-alkoxy)carbonyland (C₁-C₄-alkoxy)carbonyl-C₁-C₄-alkoxy;

or R⁹ and R¹⁰ together are a tetramethylene, pentamethylene orethyleneoxyethylene chain, each of which may carry a hydroxycarbonylgroup or a (C₁-C₆-alkoxy)carbonyl radical;

R¹¹ is hydrogen, C₁-C₈-alkyl, C₃-C₈-alkenyl or C₃-C₈-alkynyl;

R¹² and R¹³ independently of one another are each hydrogen, C₁-C₈-alkyl,C₃-C₈-alkenyl, C₃-C₈-alkynyl, C₁-C₈-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,(C₁-C₄-alkoxy)carbonyl-C₁-C₄-alkyl, C₃-C₈-cycloalkyl, phenyl orphenyl-C₁-C₄-alkyl, where the phenyl rings of the last two radicals maybe unsubstituted or may carry one to three substituents, in each caseselected from the group consisting of nitro, cyano, hydroxyl,hydroxycarbonyl, halogen, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, (C₁-C₄-alkoxy)carbonyl and(C₁-C₄-alkoxy)carbonyl-C₁-C₄-alkoxy;

R¹⁴ is C₁-C₈-alkyl;

Y and Z independently of one another are each oxygen or sulfur;

R¹⁵ is C₁-C₈-alkyl, C₁-C₈-haloalkyl or C₁-C₄-alkoxy-C₁-C₄-alkyl;

R¹⁶-R²¹ independently of one another are each hydrogen, cyano,C₁-C₈-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₈-alkoxy,C₁-C₄-alkoxy-C₁-C₄-alkoxy, hydroxycarbonyl, (C₁-C₈-alkoxy)carbonyl,aminocarbonyl, (C₁-C₈-alkyl)aminocarbonyl ordi(C₁-C₈-alkyl)aminocarbonyl;

R²²-R²⁵ independently of one another are each hydrogen, C₁-C₈-alkyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-alkenyl or C₃-C₈-alkynyl and

R²⁶-R²⁸ independently of one another are each hydrogen or C₁-C₈-alkyl;

R⁶ is hydrogen, nitro, halogen, —OR²⁹ or —CO—OR²⁹ and

R⁷ is hydrogen, nitro, halogen or —OR³⁰, where

R²⁹ and R³⁰ each have one of the meanings of R⁸,

and the agriculturally useful salts of the compounds I, except for thosecompounds I, where X is methylene and

R⁵ is —OR⁸ and R³ and R⁷ are both hydrogen or

R¹ is halogen and R³, R⁴, R⁶ and R⁷ are all simultaneously hydrogen.

Furthermore, the invention relates to

the use of the compounds I as herbicides or for thedessication/defoliation of plants,

herbicidal compositions and compositions for the dessication and/ordefoliation of plants which comprise compounds I as active ingredients,

methods for controlling undesirable vegetation and for the dessicationand/or defoliation of plants using the compounds I and

processes for preparing the compounds I and the herbicidal compositionsand compositions for the dessication and/or defoliation of plants usingthe compounds I.

EP-A 047 972 describes phenoxyalkanoic acid derivatives for increasingthe carbohydrate depositing in plants whose general formula—if thevariables are appropriately chosen—also includes compounds I where n=0,X methylene, R¹=halogen, di- or trifluoromethyl, R²=fluorine orchlorine, R³, R⁴, R⁶ and R⁷=hydrogen and R⁵=ethoxy, 2-butoxy orbut-3-en-2-yloxy, in each case substituted with a hydroxycarbonylradical or certain ester, thioester or carboxamide radicals.

Those 2-benzylpyridines I where n=0, X=methylene, R¹=halogen ortrifluoromethyl, R³, R⁴ and R⁷=hydrogen, R⁵=ethoxy, 2-butoxy orbut-3-en-2-yloxy, each of which carries a certain carboxamide group, andR⁶=hydrogen or halogen are included in the general formula of theherbicides and fungicides disclosed in DE-A 29 48 095.

The Swiss Patent CH 642 075 discloses a compound where n=0, X=methylene,R¹=chlorine, R²=hydrogen, R³, R⁴, R⁶ and R⁷=hydrogen andR⁵=2-(ethoxycarbonyl)but-2-yloxy which is said to have pharmaceuticalactivity.

Benz(o)ylpyridines of the type of the compounds I are also included inthe general formulae of the herbicides described in WO 92/22203, EP-A078 536 and EP-A 461 079.

The two benzylpyridines

where R^(a)=H (No. 20) or OC₂H₅ (No. 21) are known as inhibitors ofphotosynthesis from T. Asami et al., Biosci. Biotech. Biochem. 57(2)(1993), 350/351.

Finally, WO 96/17829 discloses certain herbicidal 3-benzoylpyridines.

The herbicidal properties of the abovementioned herbicides are, with aview to the harmful plants, not always entirely satisfactory.

It is an object of the present invention, therefore, to provide novelherbicidally active compounds which allow better selective control ofundesirable plants than known compounds. It is a further object toprovide novel compounds which have a dessicant/defoliant action.

We have found that these objects are achieved by the present substituted2-benz(o)ylpyridines of the formula I and by their herbicidal action.

Furthermore, we have found herbicidal compositions which comprise thecompounds I and have very good herbicidal activity. Moreover, we havefound processes for preparing these compositions and methods forcontrolling undesirable vegetation using the compounds I.

Furthermore, we have found that the compounds I are also suitable forthe dessication/defoliation of parts of plants, suitable plants beingcrop plants such as cotton, potatoes, oilseed rape, sunflower, soybeanor field beans, in particular cotton. In this regard, we have foundcompositions for the dessication and/or defoliation of plants, processesfor preparing these compositions and methods for the dessication and/ordefoliation of plants using the compounds I.

Depending on the substitution pattern, the compounds of the formula Ican contain one or more chiral centers, in which case they exist in theform of enantiomer or diastereomer mixtures. E/Z isomers are alsopossible provided that at least one substituent with a double bond ispresent. This invention provides the pure enantiomers or diastereomersand mixtures thereof.

Agriculturally useful salts are in particular the salts of I with thosecations and the acid addition salts of I with those acids which do notadversely affect the herbicidal or dessicant/defoliant activity of I.

Suitable cations are therefore in particular the ions of the alkalimetals, preferably sodium and potassium, of the alkaline earth metals,preferably calcium, magnesium and barium, and of the transition metals,preferably manganese, copper, zinc and iron, and the ammonium ion, whichmay carry one C₁-C₄-alkyl, phenyl or benzyl substituent and, if desired,additionally one to three further C₁-C₄-alkyl radicals, preferablydiisopropylammonium, tetramethylammonium, tetrabutylammonium,trimethylbenzylammonium, and furthermore phosphonium ions, preferablytri(C₁-C₄-alkyl)phosphonium, sulfonium ions, preferablytri(C₁-C₄-alkyl)sulfonium, and sulfoxonium ions, preferablytri-(C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily fluoride, chloride,bromide, hydrogensulfate, sulfate, dihydrogenphosphate,hydrogenphosphate, phosphate, nitrate, hydrogencarbonate, carbonate,hexafluorosilicate, hexafluorophosphate, benzoate, oxalate,dodecylbenzenesulfonate, and the anions of C₁-C₄-alkanoic acid,preferably formate, acetate, propionate and butyrate.

The organic molecular moieties mentioned for the substituents R¹, R³,R⁴, R⁵ and R⁸ to R³⁰ or as radicals on phenyl rings are collective termsfor individual listings of the individual group members. All hydrocarbonchains, ie. all the alkyl, haloalkyl, cyanoalkyl,oxetanyloxycarbonylalkyl, hydroxycarbonylalkyl, phenylalkyl,phenoxycarbonylalkyl, benzyloxycarbonylalkyl, alkoxy, haloalkoxy,alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl, haloalkenyl,cyanoalkenyl, alkenyloxy, alkynyl, haloalkynyl, cyanoalkynyl andalkynyloxy moieties can be straight-chain or branched. Halogenatedsubstituents preferably carry one to five identical or different halogenatoms.

The term halogen represents in each case fluorine, bromine, chlorine oriodine, in particular fluorine or chlorine.

Other examples of meanings are for:

C₁-C₄-alkyl: CH₃, C₂H₅, CH₂-C₂H₅, CH(CH₃)₂, n-C₄H₉, CH(CH₃)—C₂H₅,CH₂—CH(CH₃)₂ or C(CH₃)₃, in particular CH₃ or C₂H₅;

C₁-C₄-haloalkyl: a C₁-C₄-alkyl radical as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, ie. for example CH₂F, CHF₂, CF₃, CH₂Cl, CH(Cl)₂, C(Cl)₃,chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl,2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, CH₂—CHF₂,CH₂-CF₃, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, C₂F₅, 2-fluoropropyl,3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl,3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl,3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, CH₂—C₂F₅, CF₂—C₂F₅,1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl,1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutylor nonafluorobutyl, in particular CH₂F, CHF₂, CF₃, CH₂Cl, 2-fluoroethyl,2-chloroethyl or CH₂—CF₃;

C₁-C₈-alkyl: C₁-C₄-alkyl as mentioned above, or, for example, n-pentyl,1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl,1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl,1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl,1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl, in particular CH₃,C₂H₅, CH₂—C₂H₅, CH(CH₃)₂, n-butyl, C(CH₃)₃, n-pentyl or n-hexyl;

C₁-C₈-haloalkyl: a C₁-C₈-alkyl radical as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, ie. for example one of the radicals mentioned forC₁-C₄-haloalkyl, or 5-fluoro-1-pentyl, 5-chloro-1-pentyl,5-bromo-1-pentyl, 5-iodo-1-pentyl, 5,5,5-trichloro-1-pentyl,undecafluoropentyl, 6-fluoro-1-hexyl, 6-chloro-1-hexyl, 6-bromo-1-hexyl,6-iodo-1-hexyl, 6,6,6-trichloro-1-hexyl or dodecafluorohexyl, inparticular CH₂F, CHF₂, CF₃, CH₂Cl, 2-fluoroethyl, 2-chloroethyl orCH₂—CF₃;

cyano-C₁-C₈-alkyl: for example CH₂CN, 1-cyanoeth-1-yl, 2-cyanoeth-1-yl,1-cyanoprop-1-yl, 2-cyanoprop-1-yl, 3-cyanoprop-1-yl, 1-cyanoprop-2-yl,2-cyanoprop-2-yl, 1-cyanobut-1-yl, 2-cyanobut-1-yl, 3-cyanobut-1-yl,4-cyanobut-1-yl, 1-cyanobut-2-yl, 2-cyanobut-2-yl, 3-cyanobut-2-yl,4-cyanobut-2-yl, 1-cyano-2-methylprop-3-yl, 2-cyano-2-methylprop-3-yl,3-cyano-2-methylprop-3-yl, 2-(CH₂CN)prop-2-yl or 2-cyanohex-6-yl, inparticular CH₂CN or 2-cyanoethyl;

oxetan-3-yloxycarbonyl-C₁-C₄-alkyl: for exampleoxetan-3-yloxycarbonylmethyl, 2-(oxetan-3-yloxycarbonyl)ethyl,2-(oxetan-3-yloxycarbonyl)prop-1-yl,3-(oxetan-3-yloxycarbonyl)prop-1-yl, 2-(oxetan-3-yloxycarbonyl)but-1-yl,3-(oxetan-3-yloxycarbonyl)but-1-yl, 4-(oxetan-3-yloxycarbonyl)but-1-yl,1-(oxetan-3-yloxycarbonyl)but-2-yl, 3-(oxetan-3-yloxycarbonyl)but-2-yl,4-(oxetan-3-yloxycarbonyl)but-2-yl,1-(oxetan-3-yloxycarbonylmethyl)eth-1-yl,1-(oxetan-3-yloxycarbonylmethyl)-1-(methyl)eth-1-yl or1-(oxetan-3-yloxycarbonylmethyl)prop-1-yl, in particularoxetan-3-yloxycarbonylmethyl or 2-(oxetan-3-yloxycarbonyl)ethyl;

hydroxycarbonyl-C₁-C₄-alkyl: CH₂COOH, CH(CH₃)COOH, 2-(COOH)ethyl,1-(COOH)prop-1-yl, 2-(COOH)prop-1-yl, 3-(COOH)prop-1-yl,1-(COOH)but-1-yl, 2-(COOH)but-1-yl, 3-(COOH)but-1-yl, 4-(COOH)but-1-yl,1-(COOH)but-2-yl, 2-(COOH)but-2-yl, 3-(COOH)but-2-yl, 4-(COOH)but-2-yl,1-(CH₂COOH)eth-1-yl, 1-(CH₂COOH)-1-(CH₃)eth-1-yl or1-(CH₂COOH)prop-1-yl, in particular CH₂COOH or 2-(COOH)ethyl;

hydroxycarbonyl-C₁-C₈-alkyl: hydroxycarbonyl-C₁-C₄-alkyl as mentionedabove, and, for example, 5-(COOH)pent-1-yl or 6-(COOH)hex-1-yl;

phenyl-C₁-C₄-alkyl: benzyl, 1-phenylethyl, 2-phenylethyl,1-phenylprop-1-yl, 2-phenylprop-1-yl, 3-phenylprop-1-yl,1-phenylbut-1-yl, 2-phenylbut-1-yl, 3-phenylbut-1-yl, 4-phenylbut-1-yl,1-phenylbut-2-yl, 2-phenylbut-2-yl, 3-phenylbut-2-yl, 4-phenylbut-2-yl,1-(phenylmethyl)eth-1-yl, 1-(phenylmethyl)-1-(methyl)eth-1-yl or1-(phenylmethyl)prop-1-yl, in particular benzyl or 2-phenylethyl;

phenoxycarbonyl-C₁-C₄-alkyl: phenoxycarbonylmethyl,1-(phenoxycarbonyl)ethyl, 2-(phenoxycarbonyl)ethyl,1-(phenoxycarbonyl)prop-1-yl, 2-(phenoxycarbonyl)prop-1-yl,3-(phenoxycarbonyl)prop-1-yl, 1-(phenoxycarbonyl)but-1-yl,2-(phenoxycarbonyl)but-1-yl, 3-(phenoxycarbonyl)but-1-yl,4-(phenoxycarbonyl)but-1-yl, 1-(phenoxycarbonyl)but-2-yl,2-(phenoxycarbonyl)but-2-yl, 3-(phenoxycarbonyl)but-2-yl,4-(phenoxycarbonyl)but-2-yl, 1-(phenoxycarbonylmethyl)eth-1-yl,1-(phenoxycarbonylmethyl)-1-(methyl)eth-1-yl or1-(phenoxycarbonylmethyl)prop-1-yl, in particular phenoxycarbonylmethylor 2-(phenoxycarbonyl)ethyl;

benzyloxycarbonyl-C₁-C₄-alkyl: benzyloxycarbonylmethyl,1-(benzyloxycarbonyl)ethyl, 2-(benzyloxycarbonyl)ethyl,1-(benzyloxycarbonyl)prop-1-yl, 2-(benzyloxycarbonyl)prop-1-yl,3-(benzyloxycarbonyl)prop-1-yl, 1-(benzyloxycarbonyl)but-1-yl,2-(benzyloxycarbonyl)but-1-yl, 3-(benzyloxycarbonyl)but-1-yl,4-(benzyloxycarbonyl)but-1-yl, 1-(benzyloxycarbonyl)but-2-yl,2-(benzyloxycarbonyl)but-2-yl, 3-(benzyloxycarbonyl)but-2-yl,4-(benzyloxycarbonyl)but-2-yl, 1-(benzyloxycarbonylmethyl)eth-1-yl,1-(benzyloxycarbonylmethyl)-1-(methyl)eth-1-yl or1-(benzyloxycarbonylmethyl)prop-1-yl, in particularbenzyloxycarbonylmethyl or 2-(benzyloxycarbonyl)ethyl;

C₁-C₄-alkoxy: OCH₃, OC₂H₅, n-propoxy, OCH(CH₃)₂, n-butoxy,1-methylpropoxy, OCH₂—CH(CH₃)₂ or OC(CH₃)₃, in particular OCH₃ or OC₂H₅;

C₁-C₆-alkoxy: a C₁-C₄-alkoxy radical as mentioned above, or, forexample, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy,2,2-dimethylpropoxy, 1-ethylpropoxy, n-hexoxy, 1,1-dimethylpropoxy,1,2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy,4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy,1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy,3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy,1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxyor 1-ethyl-2-methylpropoxy, in particular OCH₃, OC₂H₅, OCH₂—C₂H₅,OCH(CH₃)₂, n-butoxy, OC(CH₃)₃, n-pentoxy or n-hexoxy;

C₁-C₈-alkoxy; a C₁-C₆-alkoxy radical as mentioned above, or, forexample, O(n-C₇H₁₅) or O(n-C₈H₁₇), in particular C₁-C₆-alkoxy;

C₁-C₄-haloalkoxy: a C₁-C₄-alkoxy radical as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, ie. for example OCH₂F, OCHF₂, OCF₃, OCH₂Cl, OCH(Cl)₂, OC(Cl)₃,chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy,2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, OCH₂—CHF₂,OCH₂—CF₃, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy,2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC₂F₅,2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy,2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy,2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy,3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH₂—C₂F₅, OCF₂—C₂H₅,1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy,1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy,4-bromobutoxy or n-C₄F₉, in particular 2-chloroethoxy or OCH₂—CF₃;

(C₁-C₄-alkoxy)carbonyl: CO—OCH₃, CO—OC₂H₅, CO—OCH₂—C₂H₅, CO—OCH(CH₃)₂,n-butoxycarbonyl, CO—OCH(CH₃)—C₂H₅, CO—OCH₂—CH(CH₃)₂ or CO—OC(CH₃)₃, inparticular CO—OCH₃ or CO—OC₂H₅;

(C₁-C₆-alkoxy)carbonyl: a (C₁-C₄-alkoxy)carbonyl radical as mentionedabove, or, for example, (n-pentoxy)carbonyl, 1-methylbutoxycarbonyl,2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl,2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, (n-hexoxy)carbonyl,1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl,1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl,3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl,1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl,1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl,2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl,1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl,1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl,1-ethyl-1-methylpropoxycarbonyl or 1-ethyl-2-methylpropoxycarbonyl, inparticular COOCH₃, COOC₂H₅, n-propoxycarbonyl, COOCH(CH₃)₂,n-butoxycarbonyl, COOC(CH₃)₃, n-pentoxycarbonyl or n-hexoxycarbonyl;

(C₁-C₈-alkoxy)carbonyl: a (C₁-C₆-alkoxy)carbonyl radical as mentionedabove, or, for example, CO—O(n-C₇H₁₅) or CO—O(n-C₈H₁₇), in particular(C₁-C₆-alkoxy)carbonyl;

C₁-C₄-alkylthio: SCH₃, SC₂H₅, SCH₂—C₂H₅, SCH(CH₃)₂, n-butylthio,SCH(CH₃)—C₂H₅, SCH₂—CH(CH₃)₂ or SC(CH₃)₃, in particular SCH₃ or SC₂H₅;

—C₁-C₄-alkoxy-C₁-C₄-alkyl: C₁-C₄-alkyl which is substituted byC₁-C₄-alkoxy as mentioned above, ie. for example CH₂—OCH₃, CH₂—OC₂H₅,CH₂—OCH₂—C₂H₅, CH₂—OCH(CH₃)₂, n-butoxymethyl, (1-methylpropoxy)methyl,(2-methylpropoxy)methyl, CH₂—OC(CH₃)₂, 2-(methoxy)ethyl,2-(ethoxy)ethyl, 2-(n-propoxy)ethyl, 2-(1-methylethoxy)ethyl,2-(n-butoxy)ethyl, 2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl,2-(1,1-dimethylethoxy)ethyl, 2-(methoxy)propyl, 2-(ethoxy)propyl,2-(n-propoxy)propyl, 2-(1-methylethoxy)propyl, 2-(n-butoxy)propyl,2-(1-methylpropoxy)propyl, 2-(2-methylpropoxy)propyl,2-(1,1-dimethylethoxy)propyl, 3-(methoxy)propyl, 3-(ethoxy)propyl,3-(n-propoxy)propyl, 3-(1-methylethoxy)propyl, 3-(n-butoxy)propyl,3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl,3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl,2-(n-propoxy)butyl, 2-(1-methylethoxy)butyl, 2-(n-butoxy)butyl,2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl,2-(1,1-dimethylethoxy)butyl, 3-(methoxy)butyl, 3-(ethoxy)butyl,3-(n-propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(n-butoxy)butyl,3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl,3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl,4-(n-propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(n-butoxy)butyl,4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl or4-(1,1-dimethylethoxy)butyl, in particular CH₂—OCH₃ or 2-methoxyethyl;

C₁-C₄-alkoxy-C₁-C₄-alkoxy: C₁-C₄-alkoxy which is substituted byC₁-C₄-alkoxy as mentioned above, je. for example OCH₂—OCH₃, OCH₂—OC₂H₅,OCH₂—OCH₂—C₂H₅, OCH₂—OCH(CH₃)₂, n-butoxymethoxy,(1-methylpropoxy)methoxy, (2-methylpropoxy)methoxy, OCH₂—OC(CH₃)₃,2-(methoxy)ethoxy, 2-(ethoxy)ethoxy, 2-(n-propoxy)ethoxy,2-(1-methylethoxy)ethoxy, 2-(n-butoxy)ethoxy, 2-(1-methylpropoxy)ethoxy,2-(2-methylpropoxy)ethoxy, 2-(1,1-dimethylethoxy)ethoxy,2-(methoxy)propoxy, 2-(ethoxy)propoxy, 2-(n-propoxy)propoxy,2-(1-methylethoxy)propoxy, 2-(n-butoxy)propoxy,2-(1-methylpropoxy)propoxy, 2-(2-methylpropoxy)propoxy,2-(1,1-dimethylethoxy)propoxy, 3-(methoxy)propoxy, 3-(ethoxy)propoxy,3-(n-propoxy)propoxy, 3-(1-methylethoxy)propoxy, 3-(n-butoxy)propoxy,3-(1-methylpropoxy)propoxy, 3-(2-methylpropoxy)propoxy,3-(1,1-dimethylethoxy)propoxy, 2-(methoxy)butoxy, 2-(ethoxy)butoxy,2-(n-propoxy)butoxy, 2-(1-methylethoxy)butoxy, 2-(n-butoxy)butoxy,2-(1-methylpropoxy)butoxy, 2-(2-methylpropoxy)butoxy,2-(1,1-dimethylethoxy)butoxy, 3-(methoxy)butoxy, 3-(ethoxy)butoxy,3-(n-propoxy)butoxy, 3-(1-methylethoxy)butoxy, 3-(n-butoxy)butoxy,3-(1-methylpropoxy)butoxy, 3-(2-methylpropoxy)butoxy,3-(1,1-dimethylethoxy)butoxy, 4-(methoxy)butoxy, 4-(ethoxy)butoxy,4-(n-propoxy)butoxy, 4-(1-mnethylethoxy)butoxy, 4-(n-butoxy)butoxy,4-(1-methyipropoxy)butoxy, 4-(2-methylpropoxy)butoxy or4-(1,1-dimethylethoxy)butoxy, in particular OCH₂—OCH₃ or2-methoxyethoxy;

(C₁-C₄-alkoxy)carbonyl-C₁-C₄-alkyl: C₁-C₄-alkyl which is substituted by(C₁-C₄-alkoxy)carbonyl as mentioned above, ie. for example CH₂COOCH₃,CH₂COOC₂H₅, CH(CH₃)COOCH₃ or 2-(COOCH₃)ethyl;

(C₁-C₄-alkoxy)carbonyl-C₁-C₆-alkyl: C₁-C₆-alkyl which is substituted by(C₁-C₈-alkoxy)carbonyl as mentioned above, ie. for example CH₂COOCH₃,CH₂COOC₂H₅, CH(CH₃)COOCH₃, CH(CH₃)COOC₂H₅, C(CH₃)₂COOCH₃ orC(CH₃)₂COOC₂H₅;

hydroxycarbonyl-(C₁-C₄-alkoxy) carbonyl-C₁-C₄-alkyl:(C₁-C₄-alkoxy)carbonyl-C₁-C₄-alkyl as mentioned above which carries ahydroxycarbonyl group, ie. for example CH₂—COOCH₂—COOH,CH(CH₃)—COOCH₂—COOH, CH₂—COOCH(CH₃)—COOH or CH(CH₃)—COOCH(CH₃)—COOH;

C₁-C₄-alkoxy-(C₁-C₄-alkoxy)carbonyl-C₁-C₄-alkyl:(C₁-C₄-alkoxy)carbonyl-C₁-C₄-alkyl as mentioned above which carries aC₁-C₄-alkoxy group such as OCH₃, OC₂H₅, OCH₂—C₂H₅, OCH(CH₃)₂, n-butoxy,OCH(CH₃)—C₂H₅, OCH₂—CH(CH₃)₂ and OC(CH₃)₃, ie. for exampleCH₂—COOCH₂—OCH₃, CH₂—COOCH₂—OC₂H₅, CH₂—COOCH₂—OCH(CH₃)₂,CH₂—COOCH₂—OC(CH₃)₃, CH₂—COOCH₂—CH₂—OCH₃, CH₂—COOCH₂—CH₂—OC₂H₅,CH(CH₃)—COOCH₂—CH₂—OCH₃ or CH(CH₃)—COOCH₂—CH₂—OC₂H₅, in particularCH₂—COOCH₂—CH₂—OCH3, CH₂—COOCH₂—CH₂—OC₂H₅, CH(CH₃)—COOCH₂—CH₂—OCH₃ orCH(CH₃)—COOCH₂—CH₂—OC₂H₅;

(C₁-C₄-alkoxy)carbonyl-(C₁-C₄-alkoxy)carbonyl-C₁-C₄-alkyl:(C₁-C₄-alkoxy)carbonyl-C₁-C₄-alkyl as mentioned above which carries a(C₁-C₄-alkoxy)carbonyl group such as COOCH₃, COOC₂H₅, COOCH₂—C₂H₅,COOCH(CH₃)₂, COOCH₂—(n-C₃H₇), OCH(CH₃)—C₂H₅, OCH₂—CH(CH₃)₂ and OC(CH₃)₃,ie. for example CH₂—COOCH₂—COOCH₃, CH₂—COOCH₂—COOC₂H₅,CH₂—COOCH₂—COOCH(CH₃)₂, CH₂—COOCH₂—COOC(CH₃)₃, CH₂—COOCH₂—COOCH₃,CH₂—COOCH₂—COOC₂H₅, CH(CH₃)—COOCH₂—COOCH₃, CH(CH₃)—COOCH₂—COOC₂H₅,CH₂—COOCH(CH₃)—COOCH₃, CH₂—COOCH(CH₃)—COOC₂H₅, CH(CH₃)—COOCH(CH₃)—COOCH₃or CH(CH₃)—COOCH(CH₃)—COOC₂H₅, in particular CH₂—COOCH₂—COOCH₃,CH₂—COOCH₂—COOC₂H₅, CH(CH₃)—COOCH₂—COOCH₃, CH(CH₃)—COOCH₂—COOC₂H₅,CH₂—COOCH(CH₃)—COOCH₃, CH₂—COOCH(CH₃)—COOC₂H₅, CH(CH₃)—COOCH(CH₃)—COOCH₃or CH(CH₃)—COOCH(CH₃)—COOC₂H₅;

(C₁-C₈-haloalkoxy)carbonyl-C₁-C₆-alkyl: C₁-C₆-alkyl which is substitutedby (C₁-C₈-haloalkoxy)carbonyl such as COOCH₂F, COOCHF₂, COOCF₃,COOCH₂Cl, COOCH(Cl)₂, COOC(Cl)₃, COOCHFCl, COOCF(Cl)₂, COOCF₂Cl,COOCF₂Br, COOCHF—CH₃, COOCH₂—CH₂F, COOCH₂—CH₂Cl, COOCH₂—CH₂Br,COOCH₂—CH₂I, COOCH₂—CH₂F, COOCH₂—CF₃, COOCH₂—CHFCl, COOCH₂—CF₂Cl,COOCH₂—CF(Cl)₂, COOCH₂—C(Cl)₃, COOC₂F₅, 2-fluoropropoxycarbonyl,3-fluoropropoxycarbonyl, 2-chloropropoxycarbonyl,3-chloropropoxycarbonyl, 2-bromopropoxycarbonyl, 3-bromopropoxycarbonyl,2,2-difluoropropoxycarbonyl, 2,3-difluoropropoxycarbonyl,2,3-dichloropropoxycarbonyl, COOCH₂CH₂—CF₃, COOCH₂CH₂—C(Cl)₃,COOCH₂—C₂F₅, COOCF₂—C₂F₅, 1-(CH₂F)-2-fluoroethoxycarbonyl,1-(OCH₂Cl)-2-chloroethoxycarbonyl, 1-(OCH₂Br)-2-bromoethoxycarbonyl,4-fluorobutoxycarbonyl, 4-chlorobutoxycarbonyl, 4-bromobutoxycarbonyl,COOCF₂CF₂—C₂F₅, 5-fluoropentoxycarbonyl, 5-chloropentoxycarbonyl,5-bromopentoxycarbonyl, 5-iodopentoxycarbonyl,5,5,5-trichloropentoxycarbonyl, COOCF₂—(n-C₄F₉), 6-fluorohexoxycarbonyl,6-chlorohexoxycarbonyl, 6-bromohexoxycarbonyl, 6-iodohexoxycarbonyl,6,6,6-trichlorohexoxycarbonyl and COOCF₂—(n-C₅F₁₁), ie. for exampleCH₂—COOCH₂—CF₃, CH(CH₃)—COOCH₂—CF₃, CH₂—COOCH₂—C(Cl)₃ orCH(CH₃)—COOCH₂—C(Cl)₃;

(C₁-C₄-alkoxy)carbonyl-C₁-C₄-alkoxy: C₁-C₄-alkoxy, which is substitutedby (C₁-C₄-alkoxy)carbonyl as mentioned above, ie. for exampleOCH₂COOCH₃, OCH₂COOC₂H₅, OCH₂COOCH₂—C₂H₅, OCH₂COOCH(CH₃)₂,OCH₂COOCH₂CH₂—C₂H₅, OCH₂COOCH(CH₃)—C₂H₅, OCH₂COOCH₂—CH(CH₃)₂,OCH₂COOC(CH₃)₃, OCH(CH₃)COOCH₃, OCH(CH₃)COOC₂H₅, OCH₂CH₂COOCH₃,OCH₂CH₂COOC₂H₅, OCH₂CH₂COOCH₂—C₂H₅, OCH₂CH₂COOCH(CH₃)₂,OCH₂CH₂COOCH₂CH₂—CH₂H₅, 2-[COOCH(CH₃)—C₂H₅]ethoxy,2-[COOCH₂—CH(CH₃)₂]ethoxy, OCH₂CH₂COOC(CH₃)₃, 2-(COOCH₃)propoxy,2-(COOC₂H₅)propoxy, 2-(COOCH₂—C₂H₅)propoxy, 2-[COOCH(CH₃)₂]propoxy,2-(COOCH₂CH₂—C₂H₅)propoxy, 2-[COOCH(CH₃)—C₂H₅]propoxy,2-[COOCH₂—CH(CH₃)₂]propoxy, 2-[COOC(CH₃)₃]propoxy, 3-(COOCH₃)propoxy,3-(COOC₂H₅)propoxy, 3-(COOCH₂—C₂H₅)propoxy, 3-[COOCH(CH₃)₂]propoxy,3-(COOCH₂CH₂—C₂H₅)propoxy, 3-[COOCH(CH₃)—C₂H₅]-propoxy,3-[COOCH₂—CH(CH₃)₂]propoxy, 3-[COOC(CH₃)₃]propoxy, 2-(COOCH₃)butoxy,2-(COOC₂H₅)butoxy, 2-(COOCH₂—C₂H₅)butoxy, 2-[COOCH(CH₃)₂]butoxy,2-(COOCH₂CH₂—C₂H₅)butoxy, 2-[COOCH(CH₃)—C₂H₅]]butoxy,2-[COOCH₂—CH(CH₃)₂]butoxy, 2-[COOC(CH₃)₃]butoxy, 3-(COOCH₃)butoxy,3-(COOC₂H₅)butoxy, 3-(COOCH₂—C₂H₅)butoxy, 3-[COOCH(CH₃)₂]butoxy,3-(COOCH₂CH₂—C₂H₅)butoxy, 3-[COOCH(CH₃)—C₂H₅]butoxy,3-[COOCH₂—CH(CH₃)₂]butoxy, 3-[COOC(CH₃)₃]butoxy, 4-(COOCH₃)butoxy,4-(COOC₂H₅)butoxy, 4-(COOCH₂—C₂H₅)butoxy, 4-[COOCH(CH₃)₂]butoxy,4-(COOCH₂CH₂—C₂H₅)butoxy, 4-[COOCH(CH₃)—C₂H₅]butoxy,4-[COOCH₂—CH(CH₃)₂]butoxy or 4-[1,1-COOC(CH₃)₃]butoxy, in particularOCH₂—COOCH₃, OCH₂—COOC₂H₅, OCH₂—COOCH₂—C₂H₅, OCH₂—COOCH(CH₃)₂,OCH₂—COOCH₂—CH₂—C₂H₅, OCH₂—COOCH(CH₃)—C₂H₅, OCH₂—COOCH₂—CH(CH₃)₂,OCH₂—COOCH₂—CH₂CH₂—C₂H₅, OCH(CH₃)—COOCH₃, OCH(CH₃)—COOC₂H₅,OCH(CH₃)—COOCH₂—C₂H₅, OCH(CH₃)—COOCH(CH₃)₂, OCH(CH₃)—COOCH₂—CH₂—C₂H₅,OCH(CH₃)—COOCH(CH₃)—C₂H₅, OCH(CH₃)—COOCH₂—CH(CH₃)₂, OCH(CH₃)—COOC(CH₃)₃or OCH(CH₃)—COOCH₂—CH₂CH₂—C₂H₅;

C₁-C₄-alkylthio-C₁-C₄-alkyl: C₁-C₄-alkyl which is substituted byC₁-C₄-alkylthio as mentioned above, ie. for example CH₂—SCH₃, CH₂—SC₂H₅,n-propylthiomethyl, CH₂—SCH(CH₃)₂, n-butylthiomethyl,(1-methylpropylthio)methyl, (2-methylpropylthio)methyl, CH₂—SC(CH₃)₃,2-methylthioethyl, 2-ethylthioethyl, 2-(n-propylthio)ethyl,2-(1-methylethylthio)ethyl, 2-(n-butylthio)ethyl,2-(1-methylpropylthio)ethyl, 2-(2-methylpropylthio)ethyl,2-(1,1-dimethylethylthio)ethyl, 2-(methylthio)propyl,3-(methylthio)propyl, 2-(ethylthio)propyl, 3-(ethylthio)propyl,3-(propylthio)propyl, 3-(butylthio)propyl, 4-(methylthio)butyl,4-(ethylthio)butyl, 4-(n-propylthio)butyl or 4-(n-butylthio)butyl, inparticular 2-(methylthio)ethyl;

C₁-C₄-alkylsulfinyl: SO—CH₃, SOC₂H₅, SO—CH₂—C₂H₅, SO—CH(CH₃)₂,n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl orSO—C(CH₃)₃, in particular SO—CH₃ or SO—C₂H₅;

C₁-C₄-alkylsulfinyl-C₁-C₄-alkyl: C₁-C₄-alkyl which is substituted byC₁-C₄-alkylsulfinyl as mentioned above, preferably by SO—CH₃, ie. forexample CH₂—SO—CH₃ or 2-methylsulfinylethyl;

C₁-C₄-alkylsulfonyl: SO₂—CH₃, SO₂—C₂H₅, SO₂—CH₂—C₂H₅, SO₂—CH(CH₃)₂,n-butylsulfonyl, 1-methylpropylsulfonyl, SO₂—CH₂—CH(CH₃)₂ orSO₂—C(CH₃)₃, in particular SO₂—CH₃ or SO₂—C₂H₅;

C₁-C₄-alkylsulfonyl-C₁-C₄-alkyl: C₁-C₄-alkyl which is substituted byC₁-C₄-alkylsulfonyl as mentioned above, preferably by SO₂—CH₃, ie. forexample CH₂—SO₂—CH₃ or 2-methylsulfonylethyl;

(C₁-C₈-alkyl)aminocarbonyl: for example CO—NH—CH₃, CO—NH—C₂H₅,CO—NH—CH₂—C₂H₅, CO—NH—CH(CH₃)₂, CO—NH—CH₂CH₂—C₂H₅, CO—NH—CH(CH₃)C₂H₅,CO—NH—CH₂—CH(CH₃)₂, CO—NH—C(CH₃)₃, n-pentylaminocarbonyl,1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl,3-methylbutylaminocarbonyl, 2,2-dimethylpropylaminocarbonyl,1-ethylpropylaminocarbonyl, n-hexylaminocarbonyl,1,1-dimethylpropylaminocarbonyl, 1,2-dimethylpropylaminocarbonyl,1-methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl,3-methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl,1,1-dimethylbutylaminocarbonyl, 1,2-dimethylbutylaminocarbonyl,1,3-dimethylbutylaminocarbonyl, 2,2-dimethylbutylaminocarbonyl,2,3-dimethylbutylaminocarbonyl, 3,3-dimethylbutylaminocarbonyl,1-ethylbutylaminocarbonyl, 2-ethylbutylaminocarbonyl,1,1,2-trimethylpropylaminocarbonyl, 1,2,2-trimethylpropylaminocarbonyl,1-ethyl-1-methylpropylaminocarbonyl or1-ethyl-2-methylpropylaminocarbonyl, in particular CO—NH—CH₃,CO—NH—C₂H₅, n-propylaminocarbonyl, CO—NH—CH(CH₃)₂, n-butylaminocarbonyl,CO—NH—C(CH₃)₃, n-pentylaminocarbonyl or n-hexylaminocarbonyl;

di(C₁-C₈-alkyl)aminocarbonyl: for example CO—N(CH₃)₂, CO—N(C₂H₅)₂,CO—N(CH₂—C₂H₅)₂, CO—N[CH(CH₃)₂]₂, CO—N(n-C₄H₉)₂, CO—N[CH(CH₃)—C₂H₅]₂,CO—N[CH₂—CH(CH₃)₂]₂, CO—N[C(CH₃)₃]₂, CO—N(CH₃)—C₂H₅, CO—N(CH₃)—CH₂—C₂H₅,CO—N(CH₃)—CH(CH₃)₂, CO—N(CH₃)—(n-C₄H₉), CO—N(CH₃)—CH(CH₃)—C₂H₅,CO—N(CH₃)—CH₂—CH(CH₃)₂, CO—N(CH₃)—C(CH₃)₃, CO—N(C₂H₅)—CH₂—C₂H₅,CO—N(C₂H₅)—CH(CH₃)₂, CO—N(C₂H₅)—(n-C₄H₉), CO—N(C₂H₅)—CH(CH₃)—C₂H₅,CO—N(C₂H₅)—CH₂—CH(CH₃)₂, CO—N(C₂H₅)—C(CH₃)₃,N—[CH(CH₃)₂]—N-propylaminocarbonyl, N-butyl-N-propylaminocarbonyl,N—[1-methylpropyl)—N-propylaminocarbonyl,N—[2-methylpropyl]—N-propylaminocarbonyl,N—[C(CH₃)₃]—N-propylaminocarbonyl,N-butyl-N—[1-methylethyl]aminocarbonyl,N—[CH(CH₃)₂]—N—(1-methylpropyl)aminocarbonyl,N—[CH(CH₃)₂]—N—[2-methylpropyl]aminocarbonyl,N—[C(CH₃)₃]—N—[CH(CH₃)₂]aminocarbonyl,N-butyl-N—[(1-methylpropyl]aminocarbonyl,N-butyl-N—[2-methylpropyl]aminocarbonyl,N-butyl-N—[C(CH₃)₃]aminocarbonyl,N—[1-methylpropyl]—N—[2-methylpropyl]aminocarbonyl,N—[C(CH₃)₃]—N—[1-methylpropyl]aminocarbonyl orN—[C(CH₃)₃]—N—[2-methylpropyl]aminocarbonyl, in particular CO—N(CH₃)₂ orCO—N(C₂H₅)₂;

C₃-C₈-alkenyl: for example prop-2-en-1-yl, n-buten-4-yl,1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, 2-buten-1-yl,n-penten-3-yl, n-penten-4-yl, 1-methylbut-2-en-1-yl,2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl,2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl,1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-2-en-1-yl,1-ethylprop-2-en-1-yl, n-hex-3-en-1-yl, n-hex-4-en-1-yl,n-hex-5-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl,3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl,2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl,1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl,1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl,1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl,2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-2-en-1-yl,2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-2-en-1-yl,1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl, 2-ethylbut-2-en-1-yl,2-ethylbut-3-en-1-yl, 1,1,2-trimethylprop-2-en-1-yl,1-ethyl-1-methylprop-2-en-1-yl, 1-ethyl-2-methylprop-2-en-1-yl,n-hept-2-en-1-yl, n-hept-3-en-1-yl, n-oct-2-en-1-yl or n-oct-3-en-1-yl,in particular prop-2-en-1-yl or n-buten-4-yl;

C₃-C₈-haloalkenyl: C₃-C₆-alkenyl as mentioned above which is partiallyor fully substituted by fluorine, chlorine, bromine and/or iodine, ie.for example 2-chloroallyl, 3-chloroallyl, 2,3-dichloroallyl,3,3-dichloroallyl, 2,3,3-trichloroallyl, 2,3-dichlorobut-2-enyl,2-bromoallyl, 3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl,2,3,3-tribromoallyl or 2,3-dibromobut-2-enyl, in particular2-chloroallyl or 3,3-dichloroallyl;

C₂-C₈-haloalkenyl: 1-chlorovinyl, 2-chlorovinyl, 1,2-dichlorovinyl,1,2,2-trichlorovinyl or one of the abovementioned C₃-C₈-haloalkenylradicals;

cyano-C₂-C₈-aikenyl: for example 2-cyanovinyl, 3-cyanoallyl,4-cyanobut-2-enyl, 4-cyanobut-3-enyl or 5-cyanopent-4-enyl, preferably3-cyanoallyl or 4-cyanobui-2-enyl, in particular 3-cyanoallyl;

C₂-C₄-alkenyloxy-C₁-C₄-alkyl: C₁-C₄-alkyl which is substituted byC₂-C₄-alkenyloxy such as vinyloxy, prop-2-enyloxy, but-1-en-3-yloxy,but-1-en-4-yloxy, n-but-2-enyloxy, n-but-3-enyloxy,1-methylprop-2-enyloxy or 2-methylprop-2-enyloxy—preferably by allyloxy,2-methylprop-2-en-1-yloxy, but-1-en-3-yloxy, but-1-en-4-yloxy orbut-2-en-1-yloxy—ie. for example vinyloxymethyl, allyloxymethyl,2-(allyloxy)ethyl or but-1-en-4-yloxymethyl;

(C₃-C₆-alkenyloxy)carbonyl-(C₁-C₄-alkoxy)carbonyl-C₁-C₄-alkyl:(C₁-C₄-alkoxy)carbonyl-C₁-C₄-alkyl as mentioned above which carries a(C₃-C₆-alkenyloxy)carbonyl group such as prop-1-en-1-yl-O—CO,prop-2-en-1-yl-O—CO, 1-methylethenyl-O—CO, n-buten-1-yl-O—CO,n-buten-2-yl-O—CO, n-buten-3-yl-O—CO, 1-methylprop-1-en-1-yl-O—CO,2-methylprop-1-en-1-yl-O—CO, 1-methylprop-2-en-1-yl-O—CO,2-methylprop-2-en-1-yl-O—CO, n-penten-1-yl-O—CO, n-penten-2-yl-O—CO,n-penten-3-yl-O—CO, n-penten-4-yl-O—CO, 1-methylbut-1-en-1-yl-O—CO,2-methylbut-1-en-1-yl-O—CO, 3-methylbut-1-en-1-yl-O—CO,1-methylbut-2-en-1-yl-O—CO, 2-methylbut-2-en-1-yl-O—CO,3-methylbut-2-en-1-yl-O—CO, 1-methylbut-3-en-1-yl-O—CO,2-methylbut-3-en-1-yl-O—CO, 3-methylbut-3-en-1-yl-O—CO,1,1-dimethylprop-2-en-1-yl-O—CO, 1,2-dimethylprop-1-en-1-yl-O—CO,1,2-dimethylprop-2-en-1-yl-O—CO, 1-ethylprop-1-en-2-yl-O—CO,1-ethylprop-2-en-1-yl-O—CO, n-hex-1-en-1-yl-O—CO, n-hex-2-en-1-yl-O—CO,n-hex-3-en-1-yl-O—CO, n-hex-4-en-1-yl-O—CO, n-hex-5-en-1-yl-O—CO,1-methylpent-1-en-1-yl-O—CO, 2-methylpent-1-en-1-yl-O—CO,3-methylpent-1-en-1-yl-O—CO, 4-methylpent-1-en-1-yl-O—CO,1-methylpent-2-en-1-yl-O—CO, 2-methylpent-2-en-1-yl-O—CO,3-methylpent-2-en-1-yl-O—CO, 4-methylpent-2-en-1-yl-O—CO,1-methylpent-3-en-1-yl-O—CO, 2-methylpent-3-en-1-yl-O—CO,3-methylpent-3-en-1-yl-O—CO, 4-methylpent-3-en-1-yl-O—CO,1-methylpent-4-en-1-yl-O—CO, 2-methylpent-4-en-1-yl-O—CO,3-methylpent-4-en-1-yl-O—CO, 4-methylpent-4-en-1-yl-O—CO,1,1-dimethylbut-2-en-1-yl-O—CO, 1,1-dimethylbut-3-en-1-yl-O—CO,1,2-dimethylbut-1-en-1-yl-O—CO, 1,2-dimethylbut-2-en-1-yl-O—CO,1,2-dimethylbut-3-en-1-yl-O—CO, 1,3-dimethylbut-1-en-1-yl-O—CO,1,3-dimethylbut-2-en-1-yl-O—CO, 1,3-dimethylbut-3-en-1-yl-O—CO,2,2-dimethylbut-3-en-1-yl-O—CO, 2,3-dimethylbut-1-en-1-yl-O—CO,2,3-dimethylbut-2-en-1-yl-O—CO, 2,3-dimethylbut-3-en-1-yl-O—CO,3,3-dimethylbut-1-en-1-yl-O—CO, 3,3-dimethylbut-2-en-1-yl-O—CO,1-ethylbut-1-en-1-yl-O—CO, 1-ethylbut-2-en-1-yl-O—CO,1-ethylbut-3-en-1-yl-O—CO, 2-ethylbut-1-en-1-yl-O—CO,2-ethylbut-2-en-1-yl-O—CO, 2-ethylbut-3-en-1-yl-O—CO,1,1,2-trimethylprop-2-en-1-yl-O—CO, 1-ethyl-1-methylprop-2-en-1-yl-O—CO,1-ethyl-2-methylprop-1-en-1-yl-O—CO and1-ethyl-2-methylprop-2-en-1-yl-O—CO, ie. for exampleCH₂—COOCH₂—COOCH₂—CH═CH₂, CH₂—COOCH(CH₃)—COOCH₂—CH═CH₂,CH(CH₃)—COOCH(CH₃)—COOCH₂—CH═CH₂ or CH(CH₃)—COOCH(CH₃)—COOCH₂—CH═CH₂;

(C₃-C₈-alkenyloxy)carbonyl-C₁-C₆-alkyl: C₁-C₆-alkyl which carries a(C₃-C₆-alkenyloxy)carbonyl radical—as mentioned above—or, for example,n-hept-2-en-1-yl-O—CO, n-hept-3-en-1-yl-O—CO, n-oct-2-en-1-yl-O—CO orn-oct-3-en-1-yl-O—CO, ie. for example allyloxycarbonylmethyl,2-(allyloxycarbonyl)ethyl or but-1-en-4-yloxycarbonylmethyl;

C₃-C₈-alkynyl: for example propargyl, n-but-1-yn-3-yl, n-but-1-yn-4-yl,n-but-2-yn-1-yl, n-pent-1-yn-3-yl, n-pent-1-yn-4-yl, n-pent-1-yn-5-yl,n-pent-2-yn-1-yl, n-pent-2-yn-4-yl, n-pent-2-yn-5-yl,3-methylbut-1-yn-3-yl, 3-methylbut-1-yn-4-yl, n-hex-1-yn-3-yl,n-hex-1-yn-4-yl, n-hex-1-yn-5-yl, n-hex-1-yn-6-yl, n-hex-2-yn-1-yl,n-hex-2-yn-4-yl, n-hex-2-yn-5-yl, n-hex-2-yn-6-yl, n-hex-3-yn-1-yl,n-hex-3-yn-2-yl, 3-methylpent-1-yn-3-yl, 3-methylpent-1-yn-4-yl,3-methylpent-1-yn-5-yl, 4-methylpent-2-yn-4-yl or4-methylpent-2-yn-5-yl, in particular propargyl;

C₂-C₈-haloalkynyl: ethynyl or C₃-C₆-alkynyl as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, ie. for example 1,1-difluoroprop-2-yn-1-yl,4-fluorobut-2-yn-1-yl, 4-chlorobut-2-yn-1-yl, 1,1-difluorobut-2-yn-1-yl,5-fluoropent-3-yn-1-yl or 6-fluorohex-4-yn-1-yl;

cyano-C₃-C₈-alkynyl: for example 1-cyanopropargyl, 3-cyanopropargyl,4-cyanobut-2-yn-1-yl, 5-cyanopent-3-yn-1-yl or 6-cyanohex-4-yn-1-yl;

C₂-C₄-alkynyloxy-C₁-C₄-alkyl: C₁-C₄-alkyl which is substituted byC₂-C₄-alkynyloxy such as ethynyloxy, propargyloxy, n-but-1-yn-3-yloxy,n-but-1-yn-4-yloxy and n-but-2-yn-1-yloxy, ie. for example CH₂—OC═CH,CH₂—OCH₂-C═CH or 2-(propargyloxy)ethyl;

(C₃-C₆-alkynyloxy)carbonyl-(C₁-C₄-alkoxy)carbonyl-C₁-C₄-alkyl:(C₁-C₄-alkoxy)carbonyl-C₁-C₄-alkyl as mentioned above which carries a(C₃-C₆-alkynyloxy)carbonyl group such as propargyl-O—CO,prop-2-yn-1-yl-O—CO, n-but-1-yn-1-yl-O—CO, n-but-1-yn-3-yl-O—CO,n-but-1-yn-4-yl-O—CO, n-but-2-yn-1-yl-O—CO, n-pent-1-yn-1-yl-O—CO,n-pent-1-yn-3-yl-O—CO, n-pent-1-yn-4-yl-O—CO, n-pent-1-yn-5-yl-O—CO,n-pent-2-yn-1-yl-O—CO, n-pent-2-yn-4-yl-O—CO, n-pent-2-yn-5-yl-O—CO,3-methyl-but-1-yn-3-yl-O—CO, 3-methylbut-1-yn-4-yl-O—CO,n-hex-1-yn-1-yl-O—CO, n-hex-1-yn-3-yl-O—CO, n-hex-1-yn-4-yl-O—CO,n-hex-1-yn-5-yl-O—CO, n-hex-1-yn-6-yl-O—CO, n-hex-2-yn-1-yl-O—CO,n-hex-2-yn-4-yl-O—CO, n-hex-2-yn-5-yl-O—CO, n-hex-2-yn-6-yl-O—CO,n-hex-3-yn-1-yl-O—CO, n-hex-3-yn-2-yl-O—CO, 3-methylpent-1-yn-1-yl-O—CO,3-methylpent-1-yn-3-yl-O—CO, 3-methylpent-1-yn-4-yl-O—CO,3-methylpent-1-yn-5-yl-O—CO, 4-methylpent-1-yn-1-yl-O—CO,4-methylpent-2-yn-4-yl-O—CO and 4-methylpent-2-yn-5-yl-O—CO, ie. forexample CH₂—COOCH₂—COOCH₂—CH═CH, CH₂—COOCH(CH₃)—COOCH₂—C≡CH,CH(CH₃)—COOCH₂—COOCH₂—C≡CH or CH(CH₃)—COOCH(CH₃)—COOCH₂—C≡CH;

(C₃-C₈-alkynyloxy)carbonyl-C₁-C₆-alkyl: C₁-C₆-alkyl which preferablycarries a (C₃-C₆-alkynyloxy)carbonyl radical as mentioned above, inparticular CO—OCH₂-C≡CH, but-1-yn-3-yl-O—CO, but-1-yn-4-yl-O—CO orbut-2-yn-1-yl-O—CO,

C₃-C₈-cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cycloheptyl or cyclooctyl, in particular cyclopentyl or cyclohexyl;

(C₃-C₇-cycloalkyloxy)carbonyl-C₁-C₄-alkyl: for examplecyclopropyloxycarbonylmethyl, cyclobutyloxycarbonylmethyl,cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl,cycloheptyloxycarbonylmethyl, 1-(cyclopropyloxycarbonyl)ethyl,1-(cyclobutyloxycarbonyl)ethyl, 1-(cyclopentyloxycarbonyl)ethyl,1-(cyclohexyloxycarbonyl)ethyl, 1-(cycloheptyloxycarbonyl)ethyl,2-(cyclopropyloxycarbonyl)ethyl, 2-(cyclobutylohexycarbonyl)ethyl,2-(cyclopentyloxycarbonyl)ethyl, 2-(cyclohexyloxycarbonyl)ethyl,2-(cycloheptyloxycarbonyl)ethyl, 3-(cyclopropyloxycarbonyl)propyl,3-(cyclobutyloxycarbonyl)propyl, 3-(cyclopentyloxycarbonyl)propyl,3-(cyclohexyloxycarbonyl)propyl, 3-(cycloheptyloxycarbonyl)propyl,4-(cyclopropyloxycarbonyl)butyl, 4-(cyclobutyloxycarbonyl)butyl,4-(cyclopentyloxycarbonyl)butyl, 4-(cyclohexyloxycarbonyl)butyl or4-(cycloheptyloxycarbonyl)butyl, in particularcyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl or2-(cyclopentyloxycarbonyl)ethyl;

(C₃-C₈-cycloalkyloxy)carbonyl-C₁-C₆-alkyl: for examplecyclopropyloxycarbonylmethyl, cyclobutyloxycarbonylmethyl,cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl,cycloheptyloxycarbonylmethyl, cyclooctyloxycarbonylmethyl,1-(cyclopropyloxycarbonyl)ethyl, 1-(cyclobutyloxycarbonyl)ethyl,1-(cyclopentyloxycarbonyl)ethyl, 1-(cyclohexyloxycarbonyl)-ethyl,1-(cycloheptyloxycarbonyl)ethyl, 1-(cyclooctyloxycarbonyl)ethyl,2-(cyclopropyloxycarbonyl)ethyl, 2-(cyclobutyloxycarbonyl)ethyl,2-(cyclopentyloxycarbonyl)ethyl, 2-(cyclohexyloxycarbonyl)ethyl,2-(cycloheptyloxycarbonyl)ethyl, 2-(cyclooctyloxycarbonyl)ethyl,3-(cyclopropyloxycarbonyl)propyl, 3-(cyclobutyloxycarbonyl)propyl,3-(cyclopentyloxycarbonyl)propyl, 3-(cyclohexyloxycarbonyl)propyl,3-(cycloheptyloxycarbonyl)propyl, 3-(cyclooctyloxycarbonyl)propyl,4-(cyclopropyloxycarbonyl)butyl, 4-(cyclobutyloxycarbonyl)butyl,4-(cyclopentyloxycarbonyl)butyl, 4-(cyclohexyloxycarbonyl)butyl,4-(cycloheptyloxycarbonyl)butyl, 4-(cyclooctyloxycarbonyl)butyl,5-(cyclopropyloxycarbonyl)pentyl, 5-(cyclobutyloxycarbonyl)pentyl,5-(cyclopentyloxycarbonyl)pentyl, 5-(cyclohexyloxycarbonyl)pentyl,5-(cycloheptyloxycarbonyl)pentyl, 5-(cyclooctyloxycarbonyl)pentyl,6-(cyclopropyloxycarbonyl)hexyl, 6-(cyclobutyloxycarbonyl)hexyl,6-(cyclopentyloxycarbonyl)hexyl, 6-(cyclohexyloxycarbonyl)hexyl,6-(cycloheptyloxycarbonyl)hexyl or 6-(cyclooctyloxycarbonyl)hexyl, inparticular cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl or2-(cyclopentyloxycarbonyl)ethyl;

C₅-C₈-cycloalkenyl: cyclopent-1-enyl, cyclopent-2-enyl,cyclopent-3-enyl, cyclohex-1-enyl, cyclohex-2-enyl, cyclohex-3-enyl,cyclohept-1-enyl, cyclohept-2-enyl, cyclohept3-enyl, cyclohept-4-enyl,cyclooct-1-enyl, cyclooct-2-enyl, cyclooct-3-enyl or cyclooct-4-enyl, inparticular cyclopent-1-enyl, cyclopent-2-enyl, cyclohex-1-enyl orcyclohex-2-enyl;

(C₁-C₄-alkoxy)carbonyl-C₃-C₇-cycloalkyl: for examplemethoxycarbonylcyclopentyl, ethoxycarbonylcyclopentyl,methoxycarbonylcyclohexyl or ethoxycarbonylcyclohexyl.

Preferred with a view to the use of the substituted 2-benz(o)ylpyridinesI as herbicides and/or compounds having dessicant/defoliant action arethose compounds where the variables have the following meanings, in eachcase either on their own or in combination:

is zero;

X is carbonyl or methylene, in particular methylene;

R¹ is C₁-C₄-haloalkyl, in particular trifluoromethyl;

R² is halogen, in particular chlorine;

R³ is halogen, in particular chlorine;

R⁴ is halogen, in particular chlorine;

R⁵ is —OR⁸, —CO—OR⁸, —CO—N(R⁹,R¹⁰) or —CH═N—OR¹³, in particular —OR⁸;

R⁶ is hydrogen or halogen, in particular hydrogen;

R⁷ is hydrogen or halogen, in particular hydrogen;

R⁸ is hydrogen, C₁-C₈-alkyl, C₃-C₈-alkenyl, C₃-C₈-alkynyl,hydroxycarbonyl-C₁-C₄-alkyl, (C₁-C₈-alkoxy)carbonyl-C₁-C₆-alkyl,(C₃-C₈-alkenyloxy)carbonyl-C₁-C₆-alkyl,(C₃-C₈-alkynyloxy)carbonyl-C₁-C₆-alkyl,C₁-C₄-alkoxy-(C₁-C₄-alkoxy)carbonyl-C₁-C₄-alkyl,(C₁-C₄-alkoxy)carbonyl-(C₁-C₄-alkoxy)carbonyl-C₁-C₄-alkyl,

in particular hydrogen, C₁-C₈-alkyl, C₃-C₈-alkenyl, C₃-C₈-alkynyl,(C₁-C₈-alkoxy)carbonyl-C₁-C₆-alkyl, —CH(R²²)—CO—N(R⁹,R¹⁰),—CH(R²²)—CO—CO—OR²³ or

R⁹ and R¹⁰ are each hydrogen, C₁-C₈-alkyl or(C₁-C₄-alkoxy)carbonyl-C₁-C₄-alkyl, in particular C₁-C₈-alkyl;

R¹³ is hydrogen, C₁-C₈-alkyl, C₃-C₈-alkenyl, C₃-C₈-alkynyl or(C₁-C₄-alkoxy)carbonyl-C₁-C₄-alkyl, in particular C₁-C₈-alkyl;

R²² is hydrogen, C₁-C₈-alkyl, C₃-C₈-alkenyl or C₃-C₈-alkynyl, inparticular C₁-C₈-alkyl;

R²³ is hydrogen, C₁-C₈-alkyl, C₃-C₈-alkenyl or C₃-C₈-alkynyl, inparticular C₁-C₈-alkyl;

R²⁵ is hydrogen, C₁-C₈-alkyl, C₃-C₈-alkenyl or C₃-C₈-alkynyl, inparticular C₁-C₈-alkyl.

The substituted 2-benz(o)ylpyridines of the formula I can be obtained ina variety of ways, for example by one of the following processes:

Process A

Reaction of substituted pyridines of the formula II with benzylnitrilesof the formula III in the presence of a base {cf. for example R. J.Wolters et al., J. Pharmaceut. Sciences 64, (1975) 2013; Z.-T. Huang etal., Synth. Commun. 23, (1993), 591; H. Yamanaka and S. Ohba,Heterocycles 3, (1990), 895}:

In general, the reaction is carried out in an inert solvent or diluent,in particular in a dipolar aprotic solvent, for example inN,N-dimethylformamide, N-methylpyrrolidone or in an ether such asdiethyl ether, 1,2-diethoxyethane, tetrahydrofuran and dioxane.

Suitable bases are, for example, the alkali metal hydrides, amides,carbonates and bicarbonates, and furthermore nitrogen bases such astriethylamine, pyridine and 4-dimethylaminopyridine. Additionally, it ispossible to employ the alkali metal salts of bulky alcohols such aspotassium tert-butoxide.

The reaction temperature is generally from 0 to 150° C.

In general, the reactants are employed in approximately stochiometricalamounts, but it may be advantageous to use an excess of one of thecomponents, for example to obtain as complete a conversion of the othercomponent as possible.

The substituted pyridines II and benzylnitriles III are either known,some of them even being commercially available, or they are easilyprepared by conventional methods. For the preparation of benzylnitrilesfrom benzyl halides see, for example, V. G. Telang and C. J. Smith, J.Pharm. Sci. 59, (1970), 1521.

Process B

Partial hydrolysis of compounds I where X=CH(CN), for example in conc.sulfuric acid {cf. for example R. J. Wolters et al., J. Pharm. Sci. 64,(1975), 2013}, leads to substituted 2-benz(o)ylpyridines I whereX=CH—CONH₂, the alcoholysis of which {again, cf. for example R. J.Wolters et al.} affords 2-benz(o)ylpyridines I whereX=CH—CO—O(C₁-C₄-alkyl):

The hydrolysis with conc. sulfuric acid is usually carried out at from 0to 50° C., preferably at room temperature.

The subsequent alcoholysis is preferably carried out in excess alcoholHO(C₁-C₄-alkyl) as solvent, but it is also possible to use other inertsolvents/diluents. The alcoholysis is catalyzed by mineral acids such ashydrogen chloride.

The reaction is usually carried out at from 0 to 150° C., preferably atthe boiling point of the alcohol HO(C₁-C₄-alkyl).

Process C

Hydrolysis of 2-benz(o)ylpyridines of the formula I where X is CH—CN,CH—CONH₂ or CH—CO—O(C₁-C₄-alkyl) in the presence of an aqueous acid:

Suitable acids are for example mineral acids such as hydrochloric acid,hydrobromic acid and sulfuric acid or organic acids such astrifluoroacetic acid.

The preferred solvent is water which, if desired, may be mixed with aninert cosolvent, for example acetic acid or dimethyl sulfoxide, in orderto increase the solubility of the reactants.

The reaction is usually carried out at from 0 to 150° C., preferably atthe boiling point of the solvent.

It is usually not possible to isolate the carboxylic acids which areformed as intermediates; in most instances, they spontaneouslydecarboxylate under the stated reaction conditions.

Process D

Oxidation of 2-benz(o)ylpyridines of the formula I {X=CH—CN} with oxygen(air) in the presence of a base {cf. for example M. S. Kharasch and G.Sosnovsky, Tetrahedron 3, (1958), 97; H. G. Aurich, Tetrahedron Lett.12, (1964), 657; S. S. Kulp, Org. Prep. and Proced. 2, (1970), 137; A.Donetti et al., Synthesis 1980, 1009; J. F. Wolfe et al., J. Het. Chem.24, (1987), 1061; H. Yamanaka and S. Ohba, Heterocycles 31, (1990),895}:

Suitable bases are, for example, the alkali metal hydrides, amides,carbonates and bicarbonates, and furthermore nitrogen bases such astriethylamine, pyridine and 4-dimethylaminopyridine. Additionally, it ispossible to employ the alkali metal salts of bulky alcohols such aspotassium tert-butoxie.

Suitable solvents are both protic solvents, for example alcohols such asmethanol and ethanol, and dipolar aprotic solvents, for exampledimethylsulfoxide or ether such as tetrahydrofuran and dioxane.

The reaction is usually carried out at temperatures from 0 to 50° C.,preferably at room temperature. If desired, the progress of the reactioncan be accelerated by using a phase transfer catalyst such astriethylbenzylammonium chloride.

Process E

Reduction of 2-benz(o)ylpyridines I {X=CO} with complex hydrides such asNaBH₄ and LiAlH₄ or by catalytic hydrogenation in the presence of atransition metal catalyst, for example Raney nickel or platinum/carbon,in a conventional manner {cf. for example C. Vaccher et al., J. Het.Chem. 26, (1989), 811-815; G. R. Newkome et al., J. Org. Chem. 49,(1984), 2961-2971; A. Garcia et al., Tetrahedron Lett. 34, (1993),1797-1798; M. Takeshita et al., Heterocycles 35, (1993), 879-884; M.Takemoto et al., Chem. Pharm. Bull. 42, (1994), 802-805}:

The products I where X=CH—OH can subsequently be alkylated in thepresence of a base using alkyl halides X-(C₁-C₄-alkyl), X beingchlorine, bromine or iodine {cf. for example D. E. Beattie et al., J.Med. Chem. 20, (1977), 714-718; J. Crosby et al., Tetrahedron Lett. 30,(1989), 3849-3852; S. jriuchijima et al., J. Am. Chem. Soc. 96, (1974),4280; S. Sakuraba et al., Tetrahedron: Asymmetry 4, (1993), 1457-1460;Ya. G. BaL'on et al., Ukr. Khim. Zh. (Russ. Ed.) 57, (1991), 191-195}:

Suitable bases are, for example, alkali metal hydroxides such as sodiumhydroxide, alkali metal hydrides such as sodium hydride, alkali metalamides such as sodium amide or alkali metal salts of alcohols, such aspotassium tert-butoxide.

The reaction is usually carried out in an inert solvent/diluent, bothdipolar aprotic solvents, for example N,N-dimethylformamide,dimethylsulfoxide or ethers such as diethyl ether, tetrahydrofuran and1,4-dioxane, and protic solvents, for example alcohols such astert-butanol, being suitable solvents.

The reaction is usually carried out at a temperature from 0 to 150° C.,preferably at 20 to 1000° C.

Process E

Nucleophilic benzoylation of halopyridines of the formula IV withbenzaldehydes V in the presence of a base and a catalyst {cf. forexample H. Stetter, Angew. Chem. 88, (1976), 695; A. Miyashita et al.,Chem. Pharm. bull. 38, (1990), 1147-1152; A. Miyashita et al., ibid 40,(1992), 43-48 and 2627-2631; A. Miyashita et al., ibid 42, (1994),2017-2022}:

Suitable bases are, for example, alkali metal hydrides such as sodiumhydride or alkali metal amides such as sodium amide.

Suitable solvents are, for example, dipolar aprotic solvents, forexample N,N-dimethylformamide, dimethylsulfoxide or cyclic ethers suchas tetrahydrofuran and 1,4-dioxane.

Suitable catalysts are in particular (substituted) (benz)imidazoliumsalts and (substituted) (benzo)thiazolium salts, for example1,3-dimethylimidazolium chloride, 1,3-dimethylimidazolium bromide,1,3-dimethylimidazolium iodide, 1,3-benzimidazolium chloride,1,3-benzimidazolium bromide and 1,3-dimethylbenzimidazolium iodide.

The amount of catalyst is up to 50%, preferably from 5 to 20%, based onthe molar amount of the halopyridine used.

The reaction is usually carried out at temperatures from 0 to 150° C.,preferably at temperatures from 20 to 100° C.

Process G

Reaction of halopyridines IV with benzylmagnesium halides VI orbenzylzinc halides VII, if appropriate in the presence of a transitionmetal catalyst {cf. for example E. Negishi et al., J. org. Chem. 42,(1977), 1821 and M. Kumada et al., Tetrahedron Lett. 21, (1980), 845}:

The compounds VI and VII are easily prepared from the correspondingbenzyl halides and magnesium or zinc, for example according to M.Gaudemar, Bull. Soc. Chim. Fr., 1962, p. 974.

Suitabale catalysts are in particular nickel catalysts, for exampleNi[P(phenyl)₃]₄ or Ni[P(phenyl)₃]₂Cl₂, and palladium catalysts, forexample Pd[P(phenyl)₃]₄, Pd[P(phenyl)₃]₂Cl₂,Pd[1,2-bis(diphenylphosphino)ethane]Cl₂,Pd[1,4-bis(diphenylphosphino)butane]Cl₂ orPd[1,2′-bis(diphenylphosphino)ferrocene]Cl₂.

The reaction is usually carried out in an inert organic solvent, forexample in an ether such as diethyl ether and tetrahydrofuran.

The reaction is usually carried out at from 0 to 150° C., preferablyfrom 20 to 100° C.

Process H

Oxidation of substituted 2-benz(o)ylpyridines of the formula I where nis zero in a conventional manner {cf. for example A. Albini and S.Pietra, Heterocyclic N-Oxides, CRC-Press Inc., Boca Raton, USA 1991; H.S. Mosher et al., Org. Synth. Coll. Vol. IV, 1963, p. 828; E. C. Tayloret al., Org. Synth. Coll. Vol. IV, 1963, p. 704; T. W. Bell et al., Org.Synth. 69, (1990), 226}:

The oxidizing agents conventionally used for oxidizing the pyridine ringinclude, for example, peracetic acid, trifluoroperacetic acid,perbenzoic acid, m-chloroperbenzoic acid, monopermaleic acid, magnesiummonoperphthalate, sodium perborate, Oxonee (contains peroxidisulfate),pertungstic acid and hydrogen peroxide.

Suitable solvents are, for example, water, sulfuric acid, carboxylicacids such as acetic acid and trifluoroacetic acid and halogenatedhydrocarbons such as dichloromethane and chloroform.

The oxidation usually succeeds at temperatures from 0° C. to the boilingpoint of the reaction mixture.

The oxidizing agent is usually employed in at least equimolar amounts,based on the starting material. In specific instances, a large excess ofoxidizing agent may be advantageous.

Unless stated otherwise, all the processes described above areadvantageously carried out at atmospheric pressure or under theautogenous pressure of the reaction mixture in question.

The work-up of the reaction mixtures is usually carried out in aconventional manner. Unless stated otherwise in the processes describedabove, the products of value are obtained, for example, after thedilution of the reaction solution with water by filtration,crystallization or solvent extraction, or by removing the solvent,partitioning the residue in a mixture of water and a suitable organicsolvent and work-up of the organic phase to afford the product.

The substituted 2-benz(o)ylpyridines I can be obtained as isomermixtures in the preparation; however, if desired, these can be separatedinto largely pure isomers using customary methods such ascrystallization or chromatography, including chromatography over anoptically active adsorbent. Pure optically active isomers can beprepared advantageously from suitable optically active startingmaterials.

Agriculturally useful salts of the compounds I can be formed by reactionwith a base of the corresponding cation, preferably an alkali metalhydroxide or hydride, or by reaction with an acid of the correspondinganion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid,phosphoric acid or nitric acid.

Salts of I where the metal ion is not an alkali metal ion can beprepared by cation exchange of the corresponding alkali metal salt in aconventional manner, similarly ammonium, phosphonium, sulfonium andsulfoxonium salts by means of ammonia, phosphonium, sulfonium orsulfoxonium hydroxides.

The compounds I and their agriculturally useful salts are suitable, bothin the form of isomer mixtures and in the form of the pure isomers, foruse as herbicides. The herbicidal compositions comprising I controlvegetation on non-crop areas very efficiently, especially at high ratesof application. They act against broad-leaved weeds and grass weeds incrops such as wheat, rice, maize, soya and cotton without causing anysignificant damage to the crop plants. This effect is mainly observed atlow rates of application.

Taking into account the diversity of application methods, the compoundsI, or herbicidal compositions comprising them, can additionally beemployed in a further number of crop plants for eliminating undesirableplants. Examples of suitable crops are the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis,Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napusvar. napus, Brassica napus var. napobrassica, Brassica rapa var.silvestris, Camellia sinensis, Carthamus tinctorius, Caryaillinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffeacanephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucuscarota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypiumhirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypiumvitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare,Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linumusitatissimum, Lycopersicon lycopersicum, Malus spec., Manihotesculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rustica),Olea europaea, Oryza sativa , Phaseolus lunatus, Phaseolus vulgaris,Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica,Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharumofficinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s.vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum,Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

In addition, the compounds I may also be used in crops which toleratethe action of herbicides owing to breeding, including geneticengineering methods.

Moreover, the substituted 2-benz(o)ylpyridines I are also suitable forthe desiccation and/or defoliation of plants.

As desiccants, they are suitable, in particular, for desiccating theaerial parts of crop plants such as potatoes, oilseed rape, sunflowersand soybeans. This allows completely mechanical harvesting of theseimportant crop plants.

Also of economic interest is the facilitation of harvesting, which ismade possible by dehiscence, or reduction of the adherence to the tree,both concentrated over a period of time, in citrus fruit, olives orother species and varieties of pomaceous fruit, stone fruit and nuts.The same mechanism, ie. promotion of the formation of abscission tissuebetween fruit or leaf and shoot of the plants, is also important forreadily controllable defoliation of useful plants, in particular cotton.

Moreover, shortening the period within which the individual cottonplants mature results in improved fiber quality after harvesting.

The compounds I, or the compositions comprising them, can be used forexample in the form of ready-to-spray aqueous solutions, powders,suspensions, also highly-concentrated aqueous, oily or other suspensionsor dispersions, emulsions, oil dispersions, pastes, dusts, materials forspreading, or granules, by means of spraying, atomizing, dusting,spreading or pouring. The use forms depend on the intended aims; in anycase, they should guarantee a very fine distribution of the activecompounds according to the invention.

Suitable inert auxiliaries are essentially: mineral oil fractions ofmedium to high boiling point, such as kerosene and diesel oil,furthermore coal tar oils and oils of vegetable or animal origin,aliphatic, cyclic and aromatic hydrocarbons, eg. paraffins,tetrahydronaphthalene, alkylated naphthalenes and their derivatives,alkylated benzenes and their derivatives, alcohols such as methanol,ethanol, propanol, butanol and cyclohexanol, ketones such ascyclohexanone, strongly polar solvents, eg. amines such asN-methylpyrrolidone, and water.

Aqueous use forms can be prepared from emulsion concentrates,suspensions, pastes, wettable powders or water-dispersible granules byadding water. To prepare emulsions, pastes or oil dispersions, thesubstituted 2-benz(o)ylpyridines I, either as such or dissolved in anoil or solvent, can be homogenized in water by means of a wetting agent,tackifier, dispersant or emulsifier. Alternatively, it is possible toprepare concentrates comprising active compound, wetting agent,tackifier, dispersant or emulsifier and, if desired, solvent or oil,which are suitable for dilution with water.

Suitable surfactants are the alkali metal salts, alkaline earth metalsalts and ammonium salts of aromatic sulfonic acids, eg. ligno-,phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fattyacids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ethersulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta-and octadecanols, and also of fatty alcohol glycol ethers, condensatesof sulfonated naphthalene and its derivatives with formaldehyde,condensates of naphthalene, or of the naphthalenesulfonic acids withphenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylatedisooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenylpolyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol,fatty alcohol/ethylene oxide condensates, ethoxylated castor oil,polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, laurylalcohol polyglycol ether acetate, sorbitol esters, lignin-sulfite wasteliquors or methylcellulose.

Powders, materials for spreading and dusts can be prepared by mixing orgrinding the active compounds together with a solid carrier.

Granules, eg. coated granules, impregnated granules and homogeneousgranules, can be prepared by binding the active compounds to solidcarriers. Solid carriers are mineral earths, such as silicas, silicagels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess,clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate,magnesium oxide, ground synthetic materials, fertilizers such asammonium sulfate, ammonium phosphate and ammonium nitrate, ureas, andproducts of vegetable origin, such as cereal meal, tree bark meal, woodmeal and nutshell meal, cellulose powders, or other solid carriers.

The concentrations of the active compounds I in the ready-to-usepreparations can be varied within wide ranges. In general, theformulations comprise approximately from 0.001 to 98% by weight,preferably 0.01 to 95% by weight of at least one active compound I. Theactive compounds are employed in a purity of from 90% to 100%,preferably 95% to 100% (according to the NMR spectrum).

The formulation examples which follow illustrate the preparation of suchproducts:

I. 20 parts by weight of the compound No. 2 are dissolved in a mixturecomposed of 80 parts by weight of alkylated benzene, 10 parts by weightof the adduct of 8 to 10 mol of ethylene oxide to 1 mol of oleic acidN-monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonateand 5 parts by weight of the adduct of 40 mol of ethylene oxide to 1 molof castor oil. Pouring the solution into 100,000 parts by weight ofwater and finely distributing it therein gives an aqueous dispersionwhich comprises 0.02% by weight of the active compound.

II. 20 parts by weight of the compound No. 108 are dissolved in amixture composed of 40 parts by weight of cyclohexanone, 30 parts byweight of isobutanol, 20 parts by weight of the adduct of 7 mol ofethylene oxide to 1 mol of isooctylphenol and 10 parts by weight of theadduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring thesolution into 100,000 parts by weight of water and finely distributingit therein gives an aqueous dispersion which comprises 0.02% by weightof the active compound.

III. 20 parts by weight of the active compound No. 118 are dissolved ina mixture composed of 25 parts by weight of cyclohexanone, 65 parts byweight of a mineral oil fraction of boiling point 210 to 280° C. and 10parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol ofcastor oil. Pouring the solution into 100,000 parts by weight of waterand finely distributing it therein gives an aqueous dispersion whichcomprises 0.02% by weight of the active compound.

IV. 20 parts by weight of the active compound No. 460 are mixedthoroughly with 3 parts by weight of sodiumdiisobutylnaphthalene-α-sulfonate, 17 parts by weight of the sodium saltof a lignosulfonic acid from a sulfite waste liquor and 60 parts byweight of pulverulent silica gel, and the mixture is ground in a hammermill. Finely distributing the mixture in 20,000 parts by weight of watergives a spray mixture which comprises 0.1% by weight of the activecompound.

V. 3 parts by weight of the active compound No. 369 are mixed with 97parts by weight of finely divided kaolin. This gives a dust whichcomprises 3% by weight of active compound.

VI. 20 parts by weight of the active compound No. 470 are mixedintimately with 2 parts by weight of calcium dodecylbenzenesulfonate, 8parts by weight of fatty alcohol polyglycol ether, 2 parts by weight ofthe sodium salt of a phenol/urea/formaldehyde condensate and 68 parts byweight of a paraffinic mineral oil.This gives a stable oily dispersion.

VII. 1 part by weight of the compound No. 490 is dissolved in a mixturecomposed of 70 parts by weight of cyclohexanone, 20 parts by weight ofethoxylated isooctylphenol and 10 parts by weight of ethoxylated castoroil. The mixture can then be diluted with water to the desiredconcentration of active compound. This gives a stable emulsionconcentrate.

VIII. 1 part by weight of the compound No. 491 is dissolved in a mixturecomposed of 80 parts by weight of cyclohexane and 20 parts by weight ofWettol® EM 31 (=nonionic emulsifier based on ethoxylated castor oil;BASF AG). The mixture can then be diluted with water to the desiredconcentration of active compound. This gives a stable emulsionconcentrate.

The active compounds I or the herbicidal compositions can be appliedpre- or post-emergence. If the active compounds are less well toleratedby certain crop plants, application techniques may be used in which theherbicidal compositions are sprayed, with the aid of the sprayingequipment, in such a way that they come into as little contact aspossible, if any, with the leaves of the sensitive crop plants, whilethe active compounds reach the leaves of undesirable plants growingunderneath, or the bare soil surface (post-directed, lay-by).

The rates of application of active compound I are from 0.001 to 3.0,preferably 0.01 to 1.0, kg/ha of active substance (a.s.), depending onthe control target, the season, the target plants and the growth stage.

To widen the spectrum of action and to achieve synergistic effects, thesubstituted 2-benz(o)ylpyridines I may be mixed with a large number ofrepresentatives of other herbicidal or growth-regulating active compoundgroups and then applied concomitantly. Suitable components for mixturesare, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides,aminophosphoric acid and its derivatives, aminotriazoles, anilides,aryloxy/hetaryloxyalkanoic acids and their derivatives, benzoic acid andits derivatives, benzothiadiazinones,2-(hetaroyl/aroyl)-1,3-cyclohexanediones, hetaryl aryl ketones,benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates,quinolinecarboxylic acid and its derivatives, chloroacetanilides,cyclohexane-1,3-dione derivatives, diazines, dichloropropionic acid andits derivatives, dihydrobenzofurans, dihydrofuran-3-ones,dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls,halocarboxylic acids and their derivatives, ureas, 3-phenyluracils,imidazoles, Lmidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides,oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionicesters, phenylacetic acid and its derivatives, 2-phenylpropionic acidand its derivatives, pyrazoles, phenylpyrazoles, pyridazines,pyridinecarboxylic acid and its derivatives, pyrimidyl ethers,sulfonamides, sulfonylureas, triazines, triazinones, triazolinones,triazolecarboxamides and uracils.

It may furthermore be advantageous to apply the compounds I, alone orelse concomitantly in combination with other herbicides, in the form ofa mixture with other crop protection agents, for example together withagents for controlling pests or phytopathogenic fungi or bacteria. Alsoof interest is the miscibility with mineral salt solutions, which areemployed for treating nutritional and trace element deficiencies.Non-phytotoxic oils and oil concentrates may also be added.

PREPARATION EXAMPLES Example 13-Chloro-2-[1-(4-chlorophenyl)-1-cyanomethyl]-5-trifluoromethylpyridine(Process A)

1.65 g of sodium hydride (80% suspension in mineral oil) were washedwith 30 ml of anhydrous N,N-dimethylformamide to remove the mineral oil.The resulting sodium hydride was admixed with 25 ml ofN,N-dimethylformamide and a solution of 7.6 g of 4-chlorobenzyl cyanidein 25 ml of N,N-dimethylformamide was added dropwise within 20 minutes.With evolution of gas, a red suspension was formed which was stirred fora further 15 minutes. Subsequently, 10.8 g of2,3-dichloro-5-trifluoromethylpyridine were added dropwise to thereaction mixture within 20 minutes in an exothermic reaction. After theaddition, the reaction mixture was stirred for another 20 minutes andthen stirred into 2 l of water. The product was extracted from theaqueous phase with tert-butyl methylether (three times 200 ml). Thecombined organic phases were finally dried over magnesium sulfate andthen concentrated. The crude product was purified by silica gelchromatography (eluent: cyclohexane/ethyl acetate =4:1). Yield: 6.9 g(42%) of a colorless oil; ¹H NMR (270 MHz; in CDCl₃): δ[ppm]=5.78(s,1H), 7.36 (d,2H), 7.45 (d,2H), 7.98 (s,1H), 8.84 (s,1H).

Example 23-Chloro-2-[1-(2,3-dichlorophenyl)-1-cyanomethyl]-5-trifluoromethylpyridine(Process A)

By the method of Example 1, 10.0 g of a colorless oil were obtained from1.65 g of sodium hydride suspension, 9.3 g of 2,3-dichlorobenzyl cyanideand 10.8 g of 2,3-dichloro-5-trifluoromethylpyridine. Yield: 55%; ¹H NMR(400 MHz; in CDCl₃): δ[ppm]=6.20 (s,1H), 7.30 (t,1H), 7.50-7.56 (m,2H),8.03 (s,1H), 8.78 (s,1H).

Example 32-[1Carbamoyl-1-(4-chlorophenyl)methyl]-3-chloro-5-trifluoromethylpyridine(Process B)

At 23° C., 6.0 g of3-chloro-2-[1-(4-chlorophenyl)-1-cyanomethyl]-5-trifluoromethylpyridine(prepared by the method of Example 1) were stirred in 30 ml of 96%strength sulfuric acid for 16 hours. The reaction mixture was thencarefully stirred into 200 ml of ice water during which the productcrystallized out. The solid was separated off, washed successively withwater and n-hexane and dried. Yield: 5.5 g (87%) of colorless crystals;mp.: 135-136° C.

Example 43-Chloro-2-[1-(4-chlorophenyl)-1-methoxycarbonyl-methyl]-5-trifluoromethylpyridine(Process B)

Hydrogen chloride gas was introduced into a solution of 3.0 g of2-[1-carbamoyl-1-(4-chlorophenyl)methyl]-3-chloro-5-trifluoromethylpyridine(prepared by the method of Example 3) in 100 ml of anhydrous methanolfor 5 hours. The mixture was subsequently stirred for another 16 hoursand excess hydrogen chloride was removed by passing nitrogen through themixture. The methanol was separated off and the crude product waspurified by silica gel chromatography (eluent: cyclohexane/tert-butylmethyl ether 50:1). Yield: 1.3 g (42%) of colorless crystals; mp.:103-104° C.

Example 5 3-Chloro-2-(4-chlorobenzyl)-5-trifluoromethylpyridine (ProcessC)

4.3 g of3-chloro-2-[1-(4-chlorophenyl)-1-cyanomethyl]-5-trifluoromethylpyridine(prepared by the method of Example 1) were heated under reflux in 50 mlof 47% strength aqueous hydrogen bromide solution for 3 hours and thenstirred for another 68 hours at 23° C. The reaction mixture wassubsequently poured into 500 ml of ice water. The mixture was stirredfor a further 30 minutes and the solid that had formed was separatedoff, washed with water and then dried. Yield: 3.0 g (75%) of colorlesscrystals; mp.: 54-56° C.).

Example 6 3-Chloro-2-(2,3-dichlorobenzyl)-5-trifluoromethylpyridine(Process C)

By the method of Example 5, 6.3 g of a colorless oil were obtained from7.9 g of3-chloro-2-[1-(2,3-dichlorophenyl)-1-cyanomethyl]-5-trifluoromethylpyridine(prepared by the method of Example 2). Yield: 86%; ¹H NMR (270 MHz; inCDCl₃): δ[ppm]=4.50 (s,2H), 7.02 (d,1H), 7.15 (t,1H), 7.40 (d,1H), 7.93(s,1H), 8.67 (s,1H).

Example 7 3-Chloro-2-(4-chlorobenzoyl)-5-trifluoromethylpyridine

3.0 g of sodium hydride (80% suspension in mineral oil) were washed withanhydrous dioxane to remove the mineral oil. The resulting sodiumhydride was admixed first with 100 ml of dioxane and then, under anitrogen atmosphere, successively with 21.6 g of2,3-dichloro-5-trifluoromethylpyridine, 14.1 g of p-chlorobenzaldehydeand 2.24 g of 1,3-dimethylimidazolium iodide. This reaction mixture wasstirred at 50° C. for 1 hour and at 23° C. for 65 hours. For work-up,the mixture was diluted with 200 ml of water and then concentrated tohalf its volume. The product was subsequently extracted with methylenechloride (three times 50 ml). The combined organic phases were washedwith 50 ml of water, dried over sodium sulfate and then concentrated.The crude product was purified by vacuum distillation. Yield: 22.4 g(70%) of a yellow liquid; Boiling range: 126-139° C./0.65 mbar; purity:95%; ¹H NMR (270 MHz; in CDCl₃): δ[ppm]=7.48 (d,2H), 7.79 (d,2H), 8.12(s,1H), 8.83 (s,1H).

Example 8 3-Chloro-2-(4-chlorobenzoyl)-5-trifluoromethylpyridine(Process D)

A solution of 2.0 g of3-chloro-2-[1-(4-chlorophenyl)-1-cyanomethyl]-5-trifluoromethylpyridine(prepared by the method of Example 1) in 20 ml of dimethyl sulfoxide wasadmixed with a solution of 2.0 g of potassium carbonate in 3 ml ofwater, and the mixture was then stirred at 23° C. for 3 days under air.For work-up, the reaction mixture was poured into 200 ml of water. Theproduct of value was then extracted with tert-butyl methyl ether (threetimes 80 ml). The combined organic phases were washed with water (twotimes 50 ml each), dried over sodium sulfate and finally concentrated.The resulting black oil was purified by Kugelrohr distillation underreduced pressure. Yield: 1.2 g (62%) of a light-yellow oil; boilingrange: 110-120° C. (0.3 mbar); ¹H NMR see Ex. 7.

Example 9 3-Chloro-2-(4-chlorobenzoyl)-5-trifluoromethylpyridine(Process A+D)

16.5 g of sodium hydride (80% suspension in mineral oil) were washedwith anhydrous N,N-dimethylformamide to remove the mineral oil. Thesodium hydride was then admixed with 100 ml of N,N-dimethylformamide anda solution of 37.9 g of 4-chlorobenzyl cyanide in 100 ml ofN,N-dimethylformamide was then added dropwise (exotherm). After theaddition, the mixture was stirred for another 15 minutes. 54.0 g of2,3-dichloro-5-trifluoromethylpyridine were then added dropwise to thereaction mixture which heated up considerably in the process and waskept at about 50° C. by external cooling. After the addition, themixture was stirred for another 20 hours at 23° C. Air which had beendried over blue gel was then passed through the mixture for 4 days. Forwork-up, the reaction mixture was poured into 600 ml of ice-water. Theproduct of value was then extracted with tert-butyl methyl ether (threetimes 200 ml). The combined organic phases were washed with water (twotimes 100 ml each), dried over sodium sulfate and finally concentrated.The crude product was purified by silica gel chromatography (eluent:cyclohexane/tert-butyl methyl ether 9:1). Yield: 50.1 g (62%) of alight-yellow oil; purity (GC); 94.6%; ¹H NMR see Ex. 7.

Example 103-Chloro-2-[1-(4-chlorophenyl)-1-hydroxymethyl]-5-trifluoromethylpyridine(Process E)

With ice-cooling, 0.36 g of sodium borohydride were added a little at atime to a solution of 6.0 g of3-chloro-2-(4-chlorobenzoyl)-5-trifluoromethylpyridine in 10 ml ofanhydrous ethanol. The reaction mixture was stirred at 23° C. for 20hours, after which 50 ml of 10% strength hydrochloric acid werecarefully added dropwise. The ethanol was evaporated and the product wassubsequently extracted with tert-butyl methyl ether (three times 30 ml).The combined organic phases were dried over sodium sulfate and thenconcentrated. The crude product was purified by silica gelchromatography (eluent: cyclohexane/tert-butyl methyl ether=9:1). Yield:3.6 g (60%) of a colorless oil; ¹H NMR (270 MHz; in CDCl₃): δ[ppm]=5.02(d,1H), 6.02 (d,1H), 7.33-7.41 (m,4H), 7.91 (s,1H), 8.81 (s,1H).

Example 113-Chloro-2-[1-(4-chlorophenyl)-1-methoxymethyl]-5-trifluoromethylpyridine(Process E)

0.2 g of sodium hydride (80% suspension in mineral oil) were washed withanhydrous N,N-dimethylformamide to remove the mineral oil. The sodiumhydride was initially admixed with 50 ml of N,N-dimethylformamide and asolution of 2.1 g of3-chloro-2-[1-(4-chlorophenyl)-1-hydroxymethyl]-5-trifluoromethylpyridinein 10 ml of N,N-dimethylformamide was then added dropwise. The mixturewas subsequently stirred for another 15 minutes. After the dropwiseaddition of 1.1 g of methyl iodide, the mixture was stirred at 23° C.for a further 20 hours. The reaction mixture was then poured into 200 mlof ice-water. The product was extracted from the aqueous phase usingtert-butyl methyl ether (three times 70 ml). The combined organic phaseswere washed with water (two times 50 ml each), dried over sodium sulfateand finally concentrated. The crude product was purified by silica gelchromatography (eluent: cyclohexane/tert-butyl methyl ether 100:1).Yield: 1.1 g (50%) of a colorless oil. ¹H NMR (270 MHz; in CDCl₃):δ[ppm]=3.44 (s,3H), 5.83 (s,1H), 7.33 (d,2H), 7.48 (d,2H), 7.90 (s,1H),8.85 (s,1H).

Example 12 3-Chloro-2-(4-chlorobenzoyl)-5-trifluoromethylpyridine(Process F)

With stirring, 21.6 g of 2,3-dichloro-5-trifluoromethylpyridine, 14.1 gof 4-chlorobenzaldehyde and 2.24 g of 1,3-dimethylimidazolium iodidewere added in succession to a suspension of 3.0 g of sodium hydride (80%by weight suspension in mineral oil) in 100 ml of anhydrous dioxane. Themixture was then stirred (under a nitrogen atmosphere) for 11 hours at50° C. and then for 60 hours at 22° C. The reaction mixture was dilutedwith 200 ml of water and most of the dioxane was distilled off underreduced pressure. The product was extracted from the residue withmethylene chloride (three times 100 ml). The combined organic phaseswere washed with 50 ml of water, dried over sodium sulfate and finallyconcentrated. Distillation of the residue at 0.65 mbar (boiling range:126-139° C.) gave 22.4 g of a colorless oil. Yield: 70% (purity: about95%); ¹H-NMR see Ex. 7.

Example 133-Chloro-2-[1-(2,3-dichloro-4-methoxyphenyl)-1-cyanomethyl]-5-trifluoromethylpyridine(Process A) Intermediate: 2,3-Dichloro-4-methoxybenzyl bromide

At 30° C., 55.0 g of 2,3-dichloroanisole were dissolved in 155 ml ofglacial acetic acid and admixed with 9.6 g of paraformaldehyde. 65 ml ofa 30% strength by weight solution of HBr in glacial acetic acid werethen added and the mixture was stirred at 90° C. for 5 hours. Thereaction mixture was subsequently allowed to cool and then poured into800 ml of ice-water. The crystalline crude product was separated off,washed with water and recrystallized from n-hexane. Yield: 21 g (78%) ofwhite crystals; mp.: 101-102° C.

Intermediate: 2,3-Dichloro-4-methoxybenzyl cyanide

With stirring, a solution of 68 g of 2,3-dichloro-4-methoxybenzylbromide in 220 ml of dimethyl sulfoxide was added dropwise to asuspension of 15 g of anhydrous sodium cyanide in 250 ml of anhydrousdimethyl sulfoxide. The mixture was subsequently heated to refluxtemperature for 5 hours under an atmosphere of nitrogen. After cooling,the reaction mixture was poured into 1.5 l of ice-water and theresulting solid product was separated off, washed with water andpurified by stirring with petroleum ether (at 40-60° C.). Yield: 51 g(94%) of white crystals; mp.: 118-119° C.

By the method of Example 1, 39.2 g of white crystals were obtained using38.9 g of 2,3-dichloro-5-trifluoromethylpyridine, 38.9 g of2,3-dichloro-4-methoxybenzylnitrile, 5.95 g of an 80% strength by weightsuspension of sodium hydride in mineral oil and 220 ml ofdimethylformamide. Yield: 55%; mp.: 174-176° C.

Example 143-Chloro-2-[2,3-dichloro-4-hydroxybenzyl)-5-trifluoromethylpyridine(Process C)

By method of Example 5, 20 g of product of value (white crystals) wereobtained from 38 g of3-chloro-2-[1-(2,3-dichloro-4-methoxyphenyl)-1-cyanomethyl]-5-trifluoromethylpyridine.Yield: 60%; mp.: 159-161° C.

Example 15 Methyl2-[2,3-dichloro-4-([3-chloro-5-trifluoromethylpyridin-2-yl]methyl)phenoxy]acetate

At 23° C., 2.0 g of3-chloro-2-(2,3-dichloro-4-hydroxybenzyl)-5-trifluoromethylpyridine, 1.5g of anhydrous potassium carbonate and 1.0 g of methyl bromoacetate werestirred in 60 ml of anhydrous dimethylformamide for 16 hours. Thereaction mixture was then poured into 400 ml of ice-water. The resultingsolid product was separated off, washed with water and purified bystirring in n-hexane. Yield: 2.4 g (100%; white crystals); mp.: 110-111°C.

The compounds described above and other substituted 2-benz(o)ylpyridinesI which likewise have been or can be prepared by one of the describedprocesses are listed in Tables 1 and 2 below:

TABLE 1

I {n = O; X = CH₂; R¹ = CF₃; R², R³, R⁴ = Cl; R⁵ = OR⁸; R⁶, R⁷ = H}Mp./¹H NMR (in CDCl₃) No. —R⁸ [ppm]  1 —H  2 —CH₃ 88° C.  3 —C₂H₅  4—CH₂—C₂H₅  5 —CH(CH₃)₂  6 —CH₂—CH₂—C₂H₅  7 —CH₂—CH(CH₃)₂  8—CH(CH₃)—C₂H₅  9 —C(CH₃)₃  10 —CH₂.CH₂—CH₂—C₂H₅  11 cyclopropyl  12cyclobutyl  13 cyclopentyl  14 cyclohexyl  15 —CF₃  16 —CHF₂  17 —CH₂—CN 18 —CH₂—CH₂—CN  19 —CH₂—CH₂—CH₂—CN  20 —CH₂—CH₂—CH₂—CH₂—CN  21—CH₂—OCH₃  22 —CH₂—OC₂H₅  23 —CH₂—OCH₂—C₂H₅  24 —CH₂—OCH(CH₃)₂  25—CH₂—OCH₂—CH₂—C₂H₅  26 —CH₂—OCH(CH₃)—C₂H₅  27 —CH₂—OCH₂—CH(CH₃)₂  28—CH₂—OC(CH₃)₃  29 —CH₂—OCH₂—CH₂—CH₂—C₂H₅  30 —CH₂—SCH₃  31 —CH₂—SC₂H₅ 32 —CH₂—SCH₂—C₂H₅  33 —CH₂—SCH(CH₃)₂  34 —CH₂—SCH₂—CH₂—C₂H₅  35—CH₂—SCH₂—CH(CH₃)₂  36 —CH₂—SCH(CH₃)—C₂H₅  37 —CH₂—SC(CH₃)₃  38—CH₂—SCH₂—CH₂—CH₂—C₂H₅  39 —CH₂—SO—CH₃  40 —CH₂—SO—C₂H₅  41—CH₂—SO—CH₂—C₂H₅  42 —CH₂—SO—CH(CH₃)₂  43 —CH₂—SO—CH₂—CH₂—C₂H₅  44—CH₂—SO—CH₂—CH(CH₃)₂  45 —CH₂—SO—CH(CH₃)—C₂H₅  46 —CH₂—SO—C(CH₃)₃  47—CH₂—SO—CH₂—CH₂—CH₂—C₂H₅  48 —CH₂—SO₂—CH₃  49 —CH₂—SO₂—C₂H₅  50—CH₂—SO₂—CH₂—C₂H₅  51 —CH₂—SO₂—CH(CH₃)₂  52 —CH₂—SO₂—CH₂—CH₂—C₂H₅  53—CH₂—SO₂—CH₂—CH(CH₃)₂  54 —CH₂—SO₂—CH(CH₃)—C₂H₅  55 —CH₂—SO₂—C(CH₃)₃  56—CH₂—SO₂—CH₂—CH₂—CH₂—C₂H₅  57 —CH₂—CH═CH₂ 88° C.  58 —CH(CH₃)—CH═CH₂  59—CH₂—C(CH₃)═CH₂  60 —CH₂—CH═CH—CH₃  61 —CH₂—CH═C(CH₃)₂  62—CH₂—CH₂—CH═CH₂  63 —CH₂—CH₂—CH═CH—CH₃  64 —CH₂—CH₂—C(CH₃)═CH₂  65—CH₂—CH₂—C═C(CH₃)₂  66 cyclopent-2-en-1-yl  67 cyclohex-2-en-1-yl  68—CH₂—CH═CHCl  69 —CH₂—C(Cl)═CH₂  70 —CH₂—CH═CCl₂  71 —CH₂—C(Cl)═CHCl  72—CH₂—C(Cl)═CCl₂  73 —CH₂—C≡CH 91° C.  74 —CH(CH₃)—C≡CH  75 —CH₂—C≡C—CH₃ 76 benzyl  77 o-chlorobenzyl  78 m-chlorobenzyl  79 p-chlorobenzyl  80o-methylbenzyl  81 m-methylbenzyl  82 p-methylbenzyl  83 o-(OCH₃)benzyl 84 m-(OCH₃)benzyl  85 p-(OCH₃)benzyl  86 o-(OCF₃)benzyl  87m-(OCF₃)benzyl  88 p-(OCF₃)benzyl  89

 90

 91

 92

 93

 94

 95 o-nitrophenyl  96 m-nitrophenyl  97 p-nitrophenyl  98 o-cyanophenyl 99 m-cyanophenyl 100 p-cyanophenyl 101

102

103

104

105

106

107 —CH₂—CO—OH 108 —CH₂—CO—OCH₃ 111° C.  109 —CH₂—CO—OC₂H₅ 110—CH₂—CO—OCH₂—C₂H₅ 111 —CH₂—CO—OCH(CH₃)₂ 112 —CH₂—CO—OCH₂—CH₂—C₂H₅ 113—CH₂—CO—OCH₂—CH(CH₃)₂ 114 —CH₂—CO—OCH(CH₃)—C₂H₅ 115 —CH₂—CO—OC(CH₃)₃ 116—CH₂—CO—OCH₂—CH₂—CH₂—C₂H₅ 117 —CH(CH₃)—CO—OH 118 —CH(CH₃)—CO—OCH₃ oil119 —CH(CH₃)—CO—OC₂H₅ 120 —CH(CH₃)—CO—OCH₂—C₂H₅ 121—CH(CH₃)—CO—OCH(CH₃)₂ 122 —CH(CH₃)—CO—OCH₂—CH₂—C₂H₅ 123—CH(CH₃)—CO—OCH₂—CH(CH₃)₂ 124 —CH(CH₃)—CO—OCH(CH₃)—C₂H₅ 125—CH(CH₃)—CO—OC(CH₃)₃ 126 —CH(CH₃)—CO—OCH₂—CH₂—CH₂—C₂H₅ 127—CH₂—CO—OCH₂—CH═CH₂ 128 —CH₂—CO—OCH(CH₃)—CH═CH₂ 129—CH₂—CO—OCH₂—C(CH₃)═CH₂ 130 —CH₂—CO—OCH₂—CH═CH—CH₃ 131—CH₂—CO—OCH₂—CH═C(CH₃)₂ 132 —CH₂—CO—OCH₂—CH₂—CH═C(CH₃)₂ 133—CH(CH₃)—CO—OCH₂—CH═CH₂ 134 —CH(CH₃)—CO—OCH(CH₃)—CH═CH₂ 135—CH(CH₃)—CO—OCH₂—C(CH₃)═CH₂ 136 —CH(CH₃)—CO—OCH₂—CH═CH—CH₃ 137—CH(CH₃)—CO—OCH₂—CH═C(CH₃)₂ 138 —CH(CH₃)—CO—OCH₂—CH₂—CH═C(CH₃)₂ 139—CH₂—CO—OCH₂—C≡CH 140 —CH₂—CO—OCH(CH₃)—C≡CH 141 —CH₂—CO—OCH₂—C≡C—CH₃ 142—CH(CH₃)—CO—OCH₂—C≡CH 143 —CH(CH₃)—CO—OCH(CH₃)—C≡CH 144—CH(CH₃)—CO—OCH₂—C≡C—CH₃ 145 —CH₂—CO—OCH₂—CH₂—OCH₃ 146—CH₂—CO—OCH₂—CH₂—OC₂H₅ 147 —CH₂—CO—OCH₂—CH₂—OCH₂—C₂H₅ 148—CH₂—CO—OCH₂—CH₂—OCH(CH₃)₂ 149 —CH(CH₃)—CO—OCH₂—CH₂—OCH₃ 150—CH(CH₃)—CO—OCH₂—CH₂—OC₂H₅ 151 —CH(CH₃)—CO—OCH₂—CH₂—OCH₂—C₂H₅ 152—CH(CH₃)—CO—OCH₂—CH₂—OCH(CH₃)₂ 153 —CH₂—CO—OCH₂—CF₃ 154—CH(CH₃)—CO—OCH₂—CF₃ 155 —CH₂—CO—O-cyclopropyl 156 —CH₂—CO—O-cyclobutyl157 —CH₂—CO—O-cyclopentyl 158 —CH₂—CO—O-cyclohexyl 159—CH(CH₃)—CO—O-cyclopropyl 160 —CH(CH₃)—CO—O-cyclobutyl 161—CH(CH₃)—CO—O-cyclopentyl 162 —CH(CH₃)—CO—O-cyclohexyl 163—CH₂—CO—OCH₂—CO—OCH₃ 164 —CH₂—CO—OCH₂—CO—OC₂H₅ 165—CH₂—CO—OCH(CH₃)—CO—OCH₃ 166 —CH₂—CO—OCH(CH₃)—CO—OC₂H₅ 167—CH(CH₃)—CO—OCH₂—CO—OCH₃ 168 —CH(CH₃)—CO—OCH₂—CO—OC₂H₅ 169—CH(CH₃)—CO—OCH(CH₃)—CO—OCH₃ 170 —CH(CH₃)—CO—OCH(CH₃)—CO—OC₂H₅ 171—CH₂—CO—OCH₂—CO—OCH₂—CH═CH₂ 172 —CH₂—CO—OCH(CH₃)—CO—OCH₂—CH═CH₂ 173—CH(CH₃)—CO—OCH₂—CO—OCH₂—CH═CH₂ 174 —CH(CH₃)—CO—OCH(CH₃)—CO—OCH₂—CH═CH₂175 —CH₂—CO—OCH₂—CO—OCH₂—C≡CH 176 —CH₂—CO—OCH₂—CO—OCH(CH₃)—C≡CH 177—CH₂—CO—OCH(CH₃)—CO—OCH₂—C≡CH 178 —CH₂—CO—OCH(CH₃)—CO—OCH(CH₃)—C≡CH 179—CH(CH₃)—CO—OCH₂—CO—OCH₂—C≡CH 180 —CH(CH₃)—CO—OCH₂—CO—OCH(CH₃)—C≡CH 181—CH(CH₃)—CO—OCH(CH₃)—CO—OCH₂—C≡CH 182—CH(CH₃)—CO—OCH(CH₃)—CO—OCH(CH₃)—C≡CH 183 —CH₂—CO—OCH₂—COOH 184—CH(CH₃)—CO—OCH₂—COOH 185 —CH₂—CO—OCH(CH₃)—COOH 186—CH(CH₃)—CO—OCH(CH₃)—COOH 187 —CH₂—CO—O-(oxetan-3-yl) 188—CH(CH₃)—CO—O-(oxetan-3-yl) 189 —CH₂—CO—O-phenyl 190—CH(CH₃)—CO—O-phenyl 191 —CH₂—CO—O-(o-chlorophenyl) 192—CH₂—CO—O-(m-chlorophenyl) 193 —CH₂—CO—O-(p-chlorophenyl) 194—CH(CH₃)—CO—O-(o-chlorophenyl) 195 —CH(CH₃)—CO—O-(m-chlorophenyl) 196—CH(CH₃)—CO—O-(p-chlorophenyl) 197 —CH₂—CO—O-(o-methylphenyl) 198—CH₂—CO—O-(m-methylphenyl) 199 —CH₂—CO—O-(p-methylphenyl) 200—CH(CH₃)—CO—O-(o-methylphenyl) 201 —CH(CH₃)—CO—O-(m-methylphenyl) 202—CH(CH₃)—CO—O-(p-methylphenyl) 203

204

205

206

207

208

209

210

211

212

213

214

215

216

217

218

219

220

221 —CH₂—CO—O-(o-nitrophenyl) 222 —CH₂—CO—O-(m-nitrophenyl) 223—CH₂—CO—O-(p-nitrophenyl) 224 —CH(CH₃)—CO—O-(o-nitrophenyl) 225—CH(CH₃)—CO—O-(m-nitrophenyl) 226 —CH(CH₃)—CO—O-(p-nitrophenyl) 227—CH₂—CO—O-(o-cyanophenyl) 228 —CH₂—CO—O-(m-cyanophenyl) 229—CH₂—CO—O-(p-cyanophenyl) 230 —CH(CH₃)—CO—O-(o-cyanophenyl) 231—CH(CH₃)—CO—O-(m-cyanophenyl) 232 —CH(CH₃)—CO—O-(p-cyanophenyl) 233

234

235

236

237

238

239 —CH₂—CO—OCH₂-phenyl 240 —CH(CH₃)—CO—OCH₂-phenyl 241—CH₂—CO—OCH₂-(o-chlorophenyl) 242 —CH₂—CO—OCH₂-(m-chlorophenyl) 243—CH₂—CO—OCH₂-(p-chlorophenyl) 244 —CH(CH₃)—CO—OCH₂-(o-chlorophenyl) 245—CH(CH₃)—CO—OCH₂-(m-chlorophenyl) 246 —CH(CH₃)—CO—OCH₂-(p-chlorophenyl)247 —CH₂—CO—OCH₂-(o-methylphenyl) 248 —CH₂—CO—OCH₂-(m-methylphenyl) 249—CH₂—CO—OCH₂-(p-methylphenyl) 250 —CH(CH₃)—CO—OCH₂-(o-methylphenyl) 251—CH(CH₃)—CO—OCH₂-(m-methylphenyl) 252 —CH(CH₃)—CO—OCH₂-(p-methylphenyl)253

254

255

256

257

258

259

260

261

262

263

264

265

266

267

268

269

270

271 —CH₂—CO—OCH₂-(o-nitrophenyl) 272 —CH₂—CO—OCH₂-(m-nitrophenyl) 273—CH₂—CO—OCH₂-(p-nitrophenyl) 274 —CH(CH₃)—CO—OCH₂-(o-nitrophenyl) 275—CH(CH₃)—CO—OCH₂-(m-nitrophenyl) 276 —CH(CH₃)—CO—OCH₂-(p-nitrophenyl)277 —CH₂—CO—OCH₂-(o-cyanophenyl) 278 —CH₂—CO—OCH₂-(m-cyanophenyl) 279—CH₂—CO—OCH₂-(p-cyanophenyl) 280 —CH(CH₃)—CO—OCH₂-(o-cyanophenyl) 281—CH(CH₃)—CO—OCH₂-(m-cyanophenyl) 282 —CH(CH₃)—CO—OCH₂-(p-cyanophenyl)283

284

285

286

287

288

289

290

291

292

293

294

295 —CH₂—CO—NH₂ 296 —CH(CH₃)—CO—NH₂ 297 —CH₂—CO—NH(CH₃) 298—CH(CH₃)—CO—NH(CH₃) 299 —CH₂—CO—N(CH₃)₂ 300 —CH(CH₃)—CO—N(CH₃)₂ 301—CH₂—CO—N(CH₃)—CH₂—CO—OCH₃ 302 —CH₂—CO—N(CH₃)—CH₂—CO—OC₂H₅ 303—CH₂—CO—N(CH₃)—CH(CH₃)—CO—OCH₃ 304 —CH₂—CO—N(CH₃)—CH(CH₃)—CO—OC₂H₅ 305—CH(CH₃)—CO—N(CH₃)—CH₂—CO—OCH₃ 306 —CH(CH₃)—CO—N(CH₃)—CH₂—CO—OC₂H₅ 307—CH(CH₃)—CO—N(CH₃)—CH(CH₃)—CO—OCH₃ 308—CH(CH₃)—CO—N(CH₃)—CH(CH₃)—CO—OC₂H₅ 309 —CH₂—CO—N(CH₃)-phenyl 310—CH(CH₃)—CO—N(CH₃)-phenyl 311 —CH₂—CO—NH-phenyl 312—CH(CH₃)—CO—NH-phenyl 313 —CH₂—CO—N(CH₃)—CH₂-phenyl 314—CH(CH₃)—CO—N(CH₃)—CH₂-phenyl 315 —CH₂—CO—NH—CH₂-phenyl 316—CH(CH₃)—CO—NH—CH₂-phenyl 317 —CH₂—CO-(pyrrolidin-1-yl) 318—CH(CH₃)—CO-(pyrrolidin-1-yl) 319 —CH₂—CO-(piperidin-1-yl) 320—CH(CH₃)—CO-(piperidin-1-yl) 321 —CH₂—CO-(morpholin-4-yl) 322—CH(CH₃)—CO-(morpholin-4-yl) 323

324

325

326

327 —CH₂—CO—H 328 —CH₂—CO—CH₃ 329 —CH(CH₃)—CO—H 330 —CH(CH₃)—CO—CH₃ 331—CH₂—CH═N—OH 332 —CH(CH₃)—CH═N—OH 333 —CH₂—C(CH₃)═N—OH 334—CH(CH₃)—C(CH₃)═N—OH 335 —CH₂—CH═N—OCH₃ 336 —CH(CH₃)—CH═N—OCH₃ 337—CH₂—C(CH₃)═N—OCH₃ 338 —CH(CH₃)—C(CH₃)═N—OCH₃ 339 —CH₂—CH═N—OCH₂—CH═CH₂340 —CH(CH₃)—CH═N—OCH₂—CH═CH₂ 341 —CH₂—C(CH₃)═N—OCH₂—CH═CH₂ 342—CH(CH₃)—C(CH₃)═N—OCH₂—CH═CH₂ 343 —CH₂—CH═N—OCH₂—CO—OCH₃ 344—CH₂—CH═N—OCH₂—CO—OC₂H₅ 345 —CH(CH₃)—CH═N—OCH₂—CO—OCH₃ 346—CH(CH₃)—CH═N—OCH₂—CO—OC₂H₅ 347 —CH₂—C(CH₃)═N—OCH₂—CO—OCH₃ 348—CH₂—C(CH₃)═N—OCH₂—CO—OC₂H₅ 349 —CH(CH₃)—C(CH₃)═N—OCH₂—CO—OCH₃ 350—CH(CH₃)—C(CH₃)═N—OCH₂—CO—OC₂H₅ 351 —CH₂—CH═N—OCH(CH₃)—CO—OCH₃ 352—CH₂—CH═N—OCH(CH₃)—CO—OC₂H₅ 353 —CH(CH₃)—CH═N—OCH(CH₃)—CO—OCH₃ 354—CH(CH₃)—CH═N—OCH(CH₃)—CO—OC₂H₅ 355 —CH₂—C(CH₃)═N—OCH(CH₃)—CO—OCH₃ 356—CH₂—C(CH₃)═N—OCH(CH₃)—CO—OC₂H₅ 357 —CH(CH₃)—C(CH₃)═N—OCH(CH₃)—CO—OCH₃358 —CH(CH₃)—C(CH₃)═N—OCH(CH₃)—CO—OC₂H₅ 359 —CH₂—CO—CO—OCH₃ 360—CH₂—CO—CO—OC₂H₅ 361 —CH₂—CO—CO—OCH₂—C₂H₅ 362 —CH₂—CO—CO—OCH(CH₃)₂ 363—CH₂—CO—CO—OCH₂—CH₂—C₂H₅ 364 —CH₂—CO—CO—OCH₂—CH(CH₃)₂ 365—CH₂—CO—CO—OCH(CH₃)—C₂H₅ 366 —CH₂—CO—CO—OC(CH₃)₃ 367 —CH(CH₃)—CO—CO—OCH₃368 —CH(CH₃)—CO—CO—OC₂H₅ 369

113° C.  370

371

372

373

374

375

376

377

378

379

380

381

382

383

384

385

386

387

388

389

390

391

392

393

394

395

396

397

398

399

400

401

402

403

404

405

406

407

408

419

410

411

412

TABLE 2

I {n = O; R¹ = CF₃; R² = Cl} Mp. No. X R³ R⁴ R⁵ R⁶ R⁷ [° C.] 451 CH₂ H HCl H H 56 452 C═O H H Cl H H oil 453 CH—OH H H Cl H H oil 454 CH—OCH₃ HH Cl H H oil 455 CH—CN H H Cl H H oil 456 CH—CO—NH₂ H H Cl H H 136  457CH—CO—OCH₃ H H Cl H H 104  458 CH₂ Cl Cl H H H oil 459 CH—CN Cl Cl H H Hoil 460 C═O H Br OCH₃ H H 72 461 C═O H H OCH₂—C≡CH H H 70 462 C═O H HOCH(CH₃)—CO—OCH₃ H H 89 463 CH₂ H CF₃ H H H oil 464 CH₂ H Cl Cl H H oil465 CH₂ Cl H Cl H H oil 466 CH₂ Cl H H H H oil 467 CH₂ H Cl H H H oil468 CH₂ F H H H Cl oil 469 CH₂ H H H H H oil 470 CH₂ H H NO₂ H H 74 471CH₂ H H NH₂ H H 73 472 CH—CN H Cl OCH₃ H H 100  473 C═O H Cl OCH₃ H H 83474 CH—OH H Cl OCH(CH₃)₂ H H 65 475 C═O H Cl OCH(CH₃)—C≡CH H H 95 476CH—CN H H CN H H oil 477 CH—CN F H H H Cl 106  478 C═O H Cl H H H oil479 CH—CN H Cl H H H 74 480 CH—CN Cl H H H H 60 481 CH—CN O—CH₃ H H H H58 482 CH—CN H H CH₃ H H 74 483 CH—CN Cl H Cl H H 85 484 CH—CN H Cl Cl HH oil 485 CH—CN NO₂ H H H H 94 486 CH—CN H H H H H 72 487 CH—CN H H NO₂H H 112  488 CH—CN H CF₃ H H H oil 489 CH—CN Cl Cl OCH₃ H H 176  490 C═OCl Cl OCH(CH₃)—CO—OCH₃ H H oil 491 CH₂ H H CH₃ H H 40 492 CH₂ H OH H H H83 493 CH₂ H OCH₃ H H H oil 494 CH₂ H H COOH H H 176  495 CH₂ H HCO—OCH(CH₃)₂ H H 74 496 CH₂ H H N(SO₂—CH₃)₂ H H oil 497 CH—Cl Cl Cl OCH₃H H 134  498 CH—Br Cl Cl OCH₃ H H 105  499 CH—CH₃ Cl Cl OCH₃ H H 107 500 CH₂ Cl H NH—CO—CH₃ OH H 191  501 CH₂ H H H COOH H 125  502 CH₂ H H HCO—OC₂H₅ H 41 503 CH₂ H H NO₂ COOH H 264  504 CH₂ H H NO₂ CO—OC₂H₅ H oil505 CH₂ H NO₂ H CO—OC₂H₅ H 89 506 CH₂ H H NO₂ OH H 145  507 CH₂ NO₂ H HOCH₃ H 73 508 CH₂ H OCH₃ NO₂ H H oil 509 CH₂ NO₂ H NO₂ OCH₃ H 140  510CH₂ H H H OCH₃ NO₂ 101 

USE EXAMPLES Herbicidal Activity

The herbicidal activity of the substituted 2-benz(o)ylpyridines I wasdemonstrated by the following greenhouse experiments:

The culture containers used were plastic flowerpots containing loamysand with approximately 3.0% of humus as the substrate. The seeds of thetest plants were sown separately for each species.

For the pre-emergence treatment, the active compounds, which had beensuspended or emulsified in water, were applied directly after sowing bymeans of finely distributing nozzles. The containers were irrigatedgently to promote germination and growth and subsequently covered withtransluscent plastic hoods until the plants had rooted. This covercauses uniform germination of the test plants, unless this was adverselyaffected by the active compounds.

For the post-emergence treatment, the test plants were first grown to aheight of 3 to 15 cm, depending on the plant habit, and only thentreated with the active compounds which had been suspended or emulsifiedin water. For this purpose, the test plants were either sown directlyand grown in the same containers, or they were first grown separately asseedlings and transplanted into the test containers a few days prior totreatment. The rate of application for the post-emergence treatment was0.125, 0.0625, 0.0078 or 0.0039 kg/ha of a.s. (active substance).

Depending on the species, the plants were kept at 10-25° C. or 20-35° C.The test period extended over 2 to 4 weeks. During this time, the plantswere tended, and their response to the individual treatments wasevaluated.

Evaluation was carried out using a scale from 0 to 100. 100 means noemergence of the plants, or complete destruction of at least the aerialparts, and 0 means no damage, or normal course of growth.

The plants used in the greenhouse experiments belonged to the followingspecies:

Scientific name Common name Glycine max soybeans Abutilon theophrastivelvet leaf Solanum nigrum black nightshade Polygonum persicarialadysthumb Veronica spec. speedwell

The compounds No. 118 and 369, applied post-emergence, showed a verygood herbicidal activity against Abutilon theophrasti, Solanum nigrum,Polygonum persicaria and Veronica spec. at rates of application of 7.8and 3.9 g/ha a.s.

The compound No. 460, applied post-emergence, showed very good selectiveherbicidal activity against Abutilon theophrasti, Solanum nigrum andVeronica spec. in soya crops, which were damaged only to a small extent,at rates of application of 0.125 and 0.0625 kg/ha a.s.

USE EXAMPLES Desiccant/Defoliant Activity

The test plants used were young cotton plants with 4 leaves (withoutcotyledons) which had been grown under greenhouse conditions (relativeatmospheric humidity 50 to 70%; day/night temperature 27/20° C.).

The young cotton plants were subjected to foliar treatment to runoffpoint with aqueous preparations of the active compounds (with anaddition of 0.15% by weight of the fatty alcohol alkoxide Plurafac® LF700¹), based on the spray mixture). The amount of water applied was 1000l/ha (converted). After 13 days, the number of leaves shed and thedegree of defoliation in % were determined.

No leaves were shed in the untreated control plants.

¹)a low-foam, nonionic surfactant from BASF AG

We claim:
 1. Substituted 2-benz(o)ylpyridines of the formula I

where: n is 0 or 1; X is methylene; R¹ is C₁-C₄-haloalkyl; R² ishalogen; R³ is halogen; R⁴ is halogen; R⁵ is —OR⁸, where R⁸ isC₃-C₈-alkynyl, (C₁-C₈-alkoxy)carbonyl-C₁-C₆-alkyl or

R¹³ is hydrogen, C₁-C₈-alkyl, C₃-C₈-alkenyl, C₃-C₈-alkynyl or(C₁-C₄-alkoxy)carbonyl-C₁-C₄-alkyl, and R²² and R²³ independently of oneanother are each hydrogen, C₁-C₈-alkyl, C₃-C₈-alkenyl or C₃-C₈-alkynyl;R⁶ is hydrogen or halogen, and R⁷ is hydrogen or halogen; and theagriculturally useful salts of the compounds I.
 2. A herbicidalcomposition comprising a herbicidally effective amount of at least one2-benz(o)ylpyridine of formula I or an agriculturally useful salt of I,defined in claim 1, and at least one inert liquid or solid carrier and,if desired, at least one surfactant.
 3. A composition for thedessiccation and/or defoliation of plants, comprising such an amount ofat least one 2-benz(o)ylpyridine of formula I or an agriculturallyuseful salt of I, defined in claim 1, that it acts as a dessicant and/ordefoliant, and at least one inert liquid or solid carrier and, ifdesired, at least one surfactant.
 4. A method for controllingundesirable vegetation, which comprises allowing a herbicidallyeffective amount of at least one 2-benz(o)ylpyridine of formula I or anagriculturally useful salt of I, defined in claim 1, to act on plants,their habitat or on seeds.
 5. A method for the dessication ordefoliation of plants, which comprises allowing such an amount of atleast one substituted 2-benz(o)ylpyridine of formula I or anagriculturally useful salt of I, defined in claim 1, to act on plantsthat it has a dessicant and/or defoliant action.
 6. A method as claimedin claim 5, wherein cotton is treated.
 7. A process for preparing the2-benz(o)ylpyridine of formula I defined in claim 1, which comprisesreacting a pyridine of formula II

in the presence of a base with a benzylnitrile of formula III

and hydrolyzing and decarboxylating the product where X=CH—CN by meansof an aqueous acid.